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 1M 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 1M sodium hydroxide solution (100 ml)
7. dry with materialThe organic layer was dried with magnesium sulphate
8. concentrationconcentrated in vacuo

ORD-Eintrag

ord-6221743a92d34bf18a45f9ca94f86380

Quelldatensatz

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06849649B2