Category: 874-89-5

Application of 874-89-5, A common heterocyclic compound, 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, molecular formula is C8H7NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A solution of 25.0 g (150 mmol) of 4- (hydroxymethyl) benzonitrile, 20.8 g (300 mmol) of hydroxyamine hydrochloride and 50.4 g (600 mmol) of sodium bicarbonate in 250 [ML] of methanol was heated to reflux and stirred for 20 h. The reaction mixture was cooled to rt and filtered. The solid was washed with 100 mL of methanol. The combined methanol solution was concentrated to dryness to afford [31.] 0 g (99 %) of the title compound: 1H NMR (400 Mhz, CD30D) [8] 4.63 (s, 2H), 7.39 (d, J= 8.0, 2H), 7.62 (d, J= 8.0, 2H).

The synthetic route of 874-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; WO2003/105771; (2003); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 874-89-5, The chemical industry reduces the impact on the environment during synthesis 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction was stirred at room temperature for the time specified in Table 3. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 × 8 mL). The combined organic layers were washed with water (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 4-(Hydroxymethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Khazdooz, Leila; Zarei, Amin; Aghaei, Hamidreza; Azizi, Ghobad; Gheisari, Mohammad Mehdi; Tetrahedron Letters; vol. 57; 2; (2016); p. 168 – 171;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 4-(Hydroxymethyl)benzonitrile

Example 53 N’-hydroxy-4-(hydroxymethyl)benzenecarboximidamide: A solution of hydroxylamine hydrochloride (5.2 g), 4-(hydroxymethyl)benzonitrile (5.0 g), and sodium hydrogen carbonate (12.6 g) in methanol (50 mL) was heated to reflux for 20 hours. The reaction mixture was filtered through Celite (trade name). Thus, the filtrate was concentrated to thereby give the title compound having the following physical properties. The product was used for next reaction without further purification. TLC: Rf 0.21(chloroform:methanol:aqueous ammonia = 80:10:1); NMR (CDCl3): delta 7.61 (d, J = 8.10 Hz, 2H), 7.37 (d, J = 8.10 Hz, 2H), 4.61 (s, 2H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1760071; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 874-89-5, A common heterocyclic compound, 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, molecular formula is C8H7NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Intermediates 6a-g (shown below) were synthesized from 5a-g using the following general procedure (labeled as ?a? on FIG. 1). To a round-bottom flask equipped with a stir bar was added 5a-g (1.0 eq), hydroxylamine hydrochloride (2.0 eq), NaHCO3 (4.0 eq), and methanol (5.0 mL/mmol). The reaction was refluxed and stirred in a pre-heated 75 C. oil-bath for 6 h. The reaction mixture was cooled to room temperature, and the precipitate was filtered off and washed with methanol. The filtrate was concentrated in vacuo without further purification. Example 8 Synthesis of 41 (E)-N?-hydroxy-4-(hydroxymethyl)benzimidamide (6a) (0154) The synthesis follows the general procedure described in Example 7. Yield: 70%, MP: 217-219 C. 1H NMR (400 MHz, DMSO-d6) delta =7.88-7.78 (m, 4H), 5.93 (s, 2H).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Washington University; Tu, Zhude; Rosenberg, Adam; Liu, Hui; Han, Junbin; US2019/2450; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-(Hydroxymethyl)benzonitrile

General procedure: To 16 mL of acetonitrile/water (1:1 v/v) mixture was added 0.5-1.2 mmol of the starting compound. The contents were heated at reflux with introduction of oxone (cf. entries for each case) incrementally over the entire duration of the reaction. For secondary benzyl halides, the reactions were run at room temperature. The progress of the reaction in each case was monitored by TLC analysis. After completion of the reaction, the reaction mixture was cooled to room temperature and the organic matter was extracted with ethyl acetate. The combined organic extract was dried over anhyd Na2SO4 and concentrated in vacuo. Short pad silica gel column chromatography of the residue led to isolation of the pure product.

The synthetic route of 874-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Parida, Keshaba Nanda; Jhulki, Samik; Mandal, Susovan; Moorthy, Jarugu Narasimha; Tetrahedron; vol. 68; 47; (2012); p. 9763 – 9768,6;; ; Article; Parida, Keshaba Nanda; Jhulki, Samik; Mandal, Susovan; Moorthy, Jarugu Narasimha; Tetrahedron; vol. 68; 47; (2012); p. 9763 – 9768;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 874-89-5, A common heterocyclic compound, 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, molecular formula is C8H7NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

8B. N-Hydroxy-4-hydroxymethyl-benzamidine Hydroxylamine hydrochloride (5.17 g, 75.0 mmol) and sodium bicarbonate (12.6 g, 150 mmol) were added to a solution of 4-hydroxymethyl-benzonitrile (5.0 g, 37.5 mmol) and methanol (65.0 mL). The reaction was heated to reflux for 12 hours. The reaction mixture was cooled to room temperature and the resulting slurry was filtered. The filtrate was concentrated in vacuo to give of the title compound (6.0 g, 48% yield) as an oily solid. 1H NMR (400 MHz, CD3OD) 4.60 (s, 2H), 7.36 (d, 2H), 7.59 (d, 2H).

The synthetic route of 874-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2007/270438; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 874-89-5, Quality Control of 4-(Hydroxymethyl)benzonitrile

In a 10 mL round bottom flask, 0.66 g of 4-cyanobenzyl alcohol and 2 g of diethylene glycol dimethyl ether were sequentially added.The resulting mixture was subjected to ultrasonic irradiation at 40 kHz/30 W/70 C for 30 minutes in an ultrasonic reaction apparatus. The diethylene glycol dimethyl ether was removed under reduced pressure, and recrystallized to give 0.68 g of 4-cyanobenzoic acid, yield 93%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Hydroxymethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Central South University; Xiao Fang; Xiao Yuanyuan; Zeng Ming; Li Na; Yin Lirong; (15 pag.)CN108467342; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 874-89-5,Some common heterocyclic compound, 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, molecular formula is C8H7NO, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC-MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10% solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC-MS, FT-IR, and 1H-NMR spectral data by comparing thesespectra with those of standard samples or literature data.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(Hydroxymethyl)benzonitrile, its application will become more common.

Reference:
Article; Farhadi, Saeed; Jahanara, Kosar; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 35; 3; (2014); p. 368 – 375;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H7NO

EXAMPLE 34 This example illustrates the preparation of compound 34. 4-Hydroxymethyl-benzonitrile (3.1 g, 23.3 mmoles) was combined with N,N-diisopropylethylamine (4.9 mL, 28 mmoles) in 100 mL of anhydrous THF. To this solution was added MOMCl (3.5 mL, 46.1 mmoles) and the mixture was stirred at room temperature for 16 hours. After this period a solution of NH4OH/H2O (1:1, 20 mL) was added (-MOMCl) and the solution was stirred for 15 minutes. After this period the reaction mixture was evaporated in vacuo (-THF) and the resulting mixture was extracted with DCM (3*30 mL). The combined DCM layer was dried over anhydrous Na2SO4, evaporated in vacuo, and the resulting crude product was purified using flash silica chromatography (0-20% EtOAc/Hexane) to yield 1.6 g (39% yield) of 4-Methoxymethoxymethylbenzonitrile as a colorless liquid.

According to the analysis of related databases, 874-89-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayne, Christopher D.; Johnson, Alan T.; Lu, Shao-Po; Mohan, Raju; Griffith, Ronald C.; US2003/181420; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-(Hydroxymethyl)benzonitrile

To a solution of 7-ethoxy-2,3-dihydro-2,2-dimethyl-alpha-(1-methylethyl)-5-benzofuranmethanol (1.26 g, 4.78 mmol) and 4-cyanobenzenemethanol (530 mg, 3.98 mmol) in toluene (3.5 ml) and acetic acid (2 ml) was added conc. sulfuric acid (0.53 ml, 9.95 mmol), and the mixture was stirred for 1 hour at 80C. Ethanol (35.9 ml) was added dropwise thereto at the same temperature and the mixture was stirred for 30 minutes. After cooling, the reaction mixture was poured into ice water, and washed with diisopropyl ether. The aqueous layer was neutralized with sodium hydrogen carbonate, and extracted three times with ethyl acetate. The combined organic layer was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to a basic silica gel column chromatography (hexane/ethyl acetate, 10:1 followed by 5:1), and crystallized from diisopropyl ether-hexane to give the title compound (614 mg, yield 37%). 1H NMR (CDCl3) delta 1.23 (6H, s), 1.28 (6H, s), 1.46 (3H, t, J = 7.0 Hz), 2.11 (3H, s), 2.20 (2H, s), 2.66 (2H, s), 4.18 (2H, q, J = 7.0 Hz), 5.15 (2H, s), 6.60 (1H, s), 7.34-7.42 (4H, m).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 874-89-5.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1541576; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts