Acetyl chloride → 4-Hydroxybutyl acetate

1,4-Butanediol (0.90 ml, 10.16 mmol) was added to a stirred suspension of NaH (246 mg, 10.25 mmol) in THF (20 ml) at room temperature and stirred for 30 minutes. Acetyl chloride (0.70 mL, 9.84 mmol) was then added to the thick white slurry. Following 45 minutes of stirring, the solution was diluted with diethyl ether (30 mL) and 10 w/v % K2CO3 (aq). The phases were separated and the organic phase washed with 10% K2CO3 (1×15 mL) and brine (1×15 mL). The combined aqueous phase was extracted with diethyl ether (1×30 mL). The organic phase was dried (MgSO4) and concentrated to afford 933 mg crude product as a colourless liquid. Purification by column chromatography (25 g silica, 2:1 hexanes:ethyl acetate) afforded 686 mg of acetic acid 4-hydroxy-butyl ester (51%). 1H NMR (CDCl3) δ 1.58-1.77 (m, 4H), 2.05 (s, 3H), 3.68 (t, 2H, J=6.1 Hz), 4.10 (t, 2H, J=6.4 Hz).

1. waitFollowing 45 minutes
2. stirringof stirring
3. customThe phases were separated
4. washthe organic phase washed with 10% K2CO3 (1×15 mL) and brine (1×15 mL)
5. extractionThe combined aqueous phase was extracted with diethyl ether (1×30 mL)
6. dry with materialThe organic phase was dried (MgSO4)
7. concentrationconcentrated
8. customto afford 933 mg crude product as a colourless liquid
9. customPurification by column chromatography (25 g silica, 2:1 hexanes:ethyl acetate)

ORD record

ord-81f44ff88fc84f989a4e5b48f5f9c65a

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07354932B2