Acetyl chloride → 1-(4-(Methylthio)phenyl)ethan-1-one

Temperature

0 °C

Acetyl chloride (8.2 g, 0.105 mol) is added to a suspension of AlCl3 (16 g, 0.12 mol) in dichloroethane (50 ml) cooled to 0° C.; the mixture is stirred for 15 min and a solution of thioanisole (12.4 g, 0.1 mol) in dichloroethane (20 ml) is then added dropwise; the temperature is kept below 20° C. by cooling (30 min). The mixture is stirred for a further 1 h and allowed to stand at RT overnight. The Lewis acid complex is decomposed by addition of ice water (100 ml) with cooling, the organic phase is separated in a separating funnel, and the aqueous phase is extracted a further 2 times with dichloroethane (100 ml). The combined extracts are dried over Na2SO4 sicc. and concentrated to ¼ of the starting volume. The red-brown residue (15.2 g) is washed with diethyl ether (20 ml) and hexane (20 ml): 12 g of light red (brick-red) substance result.

1. customis kept below 20° C.
2. temperatureby cooling (30 min)
3. stirringThe mixture is stirred for a further 1 h
4. waitto stand at RT overnight
5. temperaturewith cooling
6. customthe organic phase is separated in a separating funnel
7. extractionthe aqueous phase is extracted a further 2 times with dichloroethane (100 ml)
8. dry with materialThe combined extracts are dried over Na2SO4 sicc
9. concentrationand concentrated
10. washThe red-brown residue (15.2 g) is washed with diethyl ether (20 ml) and hexane (20 ml)
11. custom12 g of light red (brick-red) substance result

ORD record

ord-81864a8930494914b6d7ebd096764e73

Source dataset

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06936632B2