Sulfuric Acid → 4-Methoxybenzenesulfonyl chloride

Temperature

17 °C

To a mixture of 54.0 g (0.5 m) of anisole, 46.0 ml (0.5 m) of phosphorus oxychloride cooled to about 17° C., there was added slowly 51 g (0.525 m) of 100 percent sulfuric acid allowing the temperature to rise to approximately 29° C. at which temperature an external water bath was applied lowering the temperature to approximately 17° C. When the addition was complete, the water bath was removed and the temperature of the reaction mixture gradually rose to about 27° C. over approximately one hour and forty-five minutes. The reaction mixture was stirred overnight at ambient temperature. To the reaction mixture, 6.02 g of sodium chloride was added and the resulting mixture was heated to approximately 90° C. After approximately three and one half hours at about 90° C., the reaction mixture was cooled and poured slowly into a slurry of 500.0 g ice, 250.0 ml water and 41.6 g of sodium chloride. The solid which formed was collected by filtration, washed three times, each with 50.0 ml ice water and dried on the filter to obtain 94.9 g of 4-methoxybenzenesulfonyl chloride, a pink-white solid. The nuclear magnetic resonance spectrum was concordant with the assigned structure.

1. customto rise to approximately 29° C. at which temperature an external water bath
2. customto approximately 17° C
3. additionWhen the addition
4. customthe water bath was removed
5. additionTo the reaction mixture, 6.02 g of sodium chloride was added
6. temperaturethe resulting mixture was heated to approximately 90° C
7. waitAfter approximately three and one half hours at about 90° C.
8. temperaturethe reaction mixture was cooled
9. additionpoured slowly into a slurry of 500.0 g ice, 250.0 ml water and 41.6 g of sodium chloride
10. customThe solid which formed
11. filtrationwas collected by filtration
12. washwashed three times
13. dry with materialeach with 50.0 ml ice water and dried on the
14. filtrationfilter

ORD record

ord-8eec05ddc3124d589533718353595b01

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04874894