Ethyl 2-bromopropionate → Ethyl 2-[4-(oxan-4-yl)phenoxy]propanoate

A suspension of 8.9 g of 4-(p-hydroxyphenyl)-tetrahydropyran in 50 ml of ethanol was added to a mixture of 1.15 g of sodium in 100 ml of ethanol and the mixture was stirred for 2 hours at room temperature and was then cooled to 0° C. 7.82 ml of ethyl 2-bromo-propanoate were added to the mixture which was then allowed to return to room temperature and the mixture was refluxed for 5 hours. The mixture was evaporated to dryness and the residue was dissolved in a mixture of 100 ml of ether, 45 ml of water and 5 ml of 2N hydrochloric acid. The aqueous phase was removed by decanting and the organic phase was washed with 2N sodium hydroxide, was dried and evaporated to dryness under reduced pressure to obtain 7.9 g of ethyl 2-[p-(4-tetrahydropyranyl)-phenoxy]-propanoate with a boiling point of 138°-140° C at 0.05 mm Hg.

1. temperaturewas then cooled to 0° C
2. customto return to room temperature
3. temperaturethe mixture was refluxed for 5 hours
4. customThe mixture was evaporated to dryness
5. dissolutionthe residue was dissolved in a mixture of 100 ml of ether, 45 ml of water and 5 ml of 2N hydrochloric acid
6. customThe aqueous phase was removed
7. customby decanting
8. washthe organic phase was washed with 2N sodium hydroxide
9. customwas dried
10. customevaporated to dryness under reduced pressure

ORD record

ord-d20a8e1b3e9a4178ac3fbbabb0849de4

Source dataset

uspto-grants-1978_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04078076