Gibson, Charles S. published the artcileSyntheses with β,β’-dichlorodiethyl ether. I. Derivatives of tetrahydropyran, Computed Properties of 30431-99-3, the publication is Journal of the Chemical Society (1930), 2525-30, database is CAplus.
(ClCH2CH2)2O (I), m. -24.5°, b12 66°, b15 70°, b744 176°, with a large excess of NaI in Me2CO, gives the β,β’-diiododiethyl ether (II), b10 123.5-4°. I, CH2(CO2Et)2 and Na in EtOH, boiled 5 hrs., give Et tetrahydropyran-4,4-dicarboxylate, b12 134-5°; hydrolysis with EtOH-KOH gives 81% of the acid, which loses CO2 at 175-85°, giving 94.5% of tetrahydropyran-4-carboxylic acid (III), b15 146-7°; acid chloride, b16 85-6°; Me ester, b16 80.5-1°; Et ester, b12 82.5°; amide, m. 179°; anilide, m. 163°. I and NCCHNaCO2Et in EtOH, heated 3 hrs. and kept 12 hrs., give 33% of Et 4-cyanotetrahydropyran-4-carboxylate, b16 125°; free acid, m. 160-2°; amide, in. 158°; heating at 180-200° for 1 hr. gives 66% of 4-cyanotetrahydropyran, b10 82-3°; this could not be reduced to the amine by Na in AmOH. I and AcCHNaCO2Et gave only a small amount of high-boiling material. II gives a product b9 122.5-3.5°, which, on hydrolysis, gives III, AcOH and a trace of a ketone. No results were obtained in the Friedel-Crafts reaction with I and C6H6 or between I and KCN. I, As2O3 and NaOH gave no condensation product.
Journal of the Chemical Society published new progress about 30431-99-3. 30431-99-3 belongs to nitriles-buliding-blocks, auxiliary class Tetrahydropyran,Nitrile,Ester, name is Ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate, and the molecular formula is C9H13NO3, Computed Properties of 30431-99-3.
Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts