Butyl 3-(p-tert-butylphenoxy)-propionate → 3-p-t-Butyl-phenoxypropanol

Temperature

-5 °C

This ester 21.0 g was dissolved in 500 ml dry ether and cooled to -5° C. in an ice/acetone bath. To the cold solution was added, cautiously, a slurry of 3.5 g lithium aluminum hydride in 100 ml dry ether. After one hour the excess lithium aluminum hydride was destroyed by the cautious addition of 200 ml ethyl acetate, then 50 ml water. The solution was filtered and the filtrate partitioned between 200 ml ether-200 ml water. The organic layer was removed, dried, and evaporated to a yellow oil which was vacuum distilled (116° C./0.35 mm) over potassium carbonate to a clear colorless oil, 3-p-t-butylphenoxypropanol, 10.1 g (64%).

1. additionTo the cold solution was added
2. customAfter one hour the excess lithium aluminum hydride was destroyed by the cautious addition of 200 ml ethyl acetate
3. filtrationThe solution was filtered
4. customthe filtrate partitioned between 200 ml ether-200 ml water
5. customThe organic layer was removed
6. customdried
7. customevaporated to a yellow oil which
8. distillationdistilled (116° C./0.35 mm) over potassium carbonate to a clear colorless oil, 3-p-t-butylphenoxypropanol, 10.1 g (64%)

ORD record

ord-ecbfde36926647cf954d8fa5ef59a520

Source dataset

uspto-grants-1989_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04816491