3,4-dihydro-2H-pyran → HCID 14523530, compound

In 70 ml of a mixed solvent of methylene chloride and THF were dissolved 5 g of p-bromomethylbenzoic acid, 10 g of dihydropyran and 585 mg of pyridinium p-toluenesulfonate, and reaction was carried out at room temperature for 6 hours. The reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, and was concentrated and recrystallized from an n-hexane/ethyl acetate/chloroform mixed solvent to obtain 4.0 g of tetrahydropyranyl p-bromomethylbenzoate. Then, 267 mg of sodium hydride washed with n-pentane was dissolved in 10 ml of DMF, and a solution of 2 g of tetrahydropyranyl p-bromomethylbenzoate and 1.86 g of p-hydroxyphenyl decylcarboxylate in 10 ml of DMF was dropped into the above solution in a nitrogen atmosphere. The mixture was stirred overnight, and the reaction liquid was put in an ice cooled 1N aqueous hydrochloric acid solution and extracted with chloroform. The extract was concentrated, the concentrate was diluted with ethanol, 170 mg of pyridinium p-toluenesulfonate was added to the dilution, and the mixture was stirred at 55° C. for 1 hour. The mixture was diluted with chloroform and the dilution was washed with a saturated aqueous sodium chloride solution concentrated and recrystallized from a mixed solvent of acetate and chloroform to obtain 1.2 g of p-decylcarboxyphenyl-p'-carboxybenzyl ether.

1. washThe reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
2. concentrationwas concentrated
3. customrecrystallized from an n-hexane/ethyl acetate/chloroform mixed solvent

ORD record

ord-b4942236263b498187633f96252058ce

Source dataset

uspto-grants-1991_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05045228