Chlorosulfonic acid → 4-Methoxy-2,6-dimethylbenzene-1-sulfonyl chloride

Chlorosulfonic acid (12 ml, 184 mmol) in methylene chloride (60 ml) was slowly added dropwise to a solution, cooled to 0° C., of 3,5-dimethylanisole (5 g, 36.71 mmol) in methylene chloride (60 ml) over the course of 10 min. The reaction mixture was stirred for a further 10 min and subsequently slowly added dropwise to ice-water (300 ml) and the mixture was stirred until the ice had melted. The phases were separated and the aqueous phase was extracted with methylene chloride (50 ml). The combined organic phases were washed with saturated sodium chloride solution (50 ml), dried (Na2SO4) and concentrated in vacuo. It may be noted that the ratio of anisole/chlorosulfuric acid can be reduced to 1/2.3 without losses with respect to the yield.

1. customThe phases were separated
2. extractionthe aqueous phase was extracted with methylene chloride (50 ml)
3. washThe combined organic phases were washed with saturated sodium chloride solution (50 ml)
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated in vacuo

ORD record

ord-1fa3c8c568dd463b8106de6a27a17e3f

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119805B2