Sulfuric Acid → 4-Methoxybenzenesulfonyl chloride

Temperature

29 °C

With stirring 51.5 g (0.525 m) of 100 percent sulfuric acid was added to a mixture of 54.0 g (0.5 m) of anisole and 46.0 ml (0.5 m) of phosphorus oxychloride maintaining a temperature of less than 5° C. by means of an ice-water bath. The ice-water bath was removed and the reaction mixture was allowed to warm to approximately 29° C. over approximately ninety minutes. Over approximately twenty minutes, the reaction mixture was heated to about 95° C. and maintained approximately two hours. After cooling the reaction mixture was poured slowly into a mixture of 501.0 g ice, 250.0 ml water and 31.0 g of sodium chloride keeping the temperature under 11° C. The resulting solid was collected by filtration, washed three times, each with 50.0 ml of ice water and dried to obtain 103.25 g of 4-methoxybenzenesulfonyl chloride, a pink-white solid. The nuclear magnetic resonance spectrum was in accord with the assigned structures.

1. customThe ice-water bath was removed
2. waitOver approximately twenty minutes
3. temperaturethe reaction mixture was heated to about 95° C.
4. temperaturemaintained approximately two hours
5. temperatureAfter cooling the reaction mixture
6. additionwas poured slowly into a mixture of 501.0 g ice, 250.0 ml water and 31.0 g of sodium chloride keeping the temperature under 11° C
7. filtrationThe resulting solid was collected by filtration
8. washwashed three times
9. dry with materialeach with 50.0 ml of ice water and dried

ORD record

ord-03a421bdda0e4b0e8803abdda6d7ac23

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04874894