Ethyl phenylacetate → Ethyl 4-(1-hydroxyundecyl)phenylacetate

Temperature

50 °C

To a solution of ethyl phenylacetate (13.1 g, 0.08 mol) and aluminium chloride (24.5 g, 0.18 mol) was added undecanoyl chloride (20 ml) at -10° C. The reaction mixture was stirred for 20 minutes at room temperature and further for 4 hours at 50° C., and then poured into the mixture of concentrated hydrochloric acid (40 ml) and ice (160 g). The resultant precipitate was extracted with ethyl acetate, and the organic layer was washed with water, dried and concentrated under reduced pressure. The resulting residue was dissolved in ethanol (100 ml), to which was added sodium borohydride (1.18 g, 0.03 mol). The reaction mixture was stirred at room temperature, to which was added 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: hexane:ethyl acetate=5:1) to obtain ethyl 4-(1-hydroxyundecyl)phenylacetate (3-v, 10.9 g, 41%) as oil.

1. extractionThe resultant precipitate was extracted with ethyl acetate
2. washthe organic layer was washed with water
3. customdried
4. concentrationconcentrated under reduced pressure
5. dissolutionThe resulting residue was dissolved in ethanol (100 ml), to which
6. stirringThe reaction mixture was stirred at room temperature, to which
7. extractionthe mixture was extracted with ethyl acetate
8. washThe organic layer was washed with water
9. customdried
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by silica gel chromatography (developing solvent: hexane:ethyl acetate=5:1)

ORD record

ord-cdf4c502105c417e9f71cb4baa820839

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04925868