Acetyl chloride → Methyl 3-(4-chlorophenyl)propanoate

To a stirred solution of 3-(4-chlorophenyl)propanoic acid (commercially available from Maybridge) (14.5 g, 77.1 mmol) in methanol (400 ml) was added acetyl chloride (50 ml) and the reaction mixture was refluxed for 20 h. After this time the reaction mixture was left to cool before being concentrated under reduced pressure. The residue was then dissolved in DCM (200 ml) and washed with 1 M sodium hydroxide solution (100 ml). The organic layer was dried with magnesium sulphate and concentrated in vacuo to give the title product as a brown oil (15.7 g, 77 mmol, 100%); 1HNMR (400 MHz, CDCl3) δ: 2.55 (t, 2H), 2.9 (t, 2H), 3.6 (s, 3H), 7.1 (d, 2H), 7.2 (d, 2H).

1. temperaturethe reaction mixture was refluxed for 20 h
2. waitAfter this time the reaction mixture was left
3. temperatureto cool
4. concentrationbefore being concentrated under reduced pressure
5. dissolutionThe residue was then dissolved in DCM (200 ml)
6. washwashed with 1 M sodium hydroxide solution (100 ml)
7. dry with materialThe organic layer was dried with magnesium sulphate
8. concentrationconcentrated in vacuo

ORD record

ord-0543a34c921447a59d89754fb2f05295

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06660756B2