Acetic Acid → 4-Ethyl-1,2-benzenediol

A mixture of 10.0 g (60.2 mM) of 4-ethylveratrole, 38.4 g (639 mM) of acetic acid and 115.0 g (668 mM) of 47% hydrobromic acid was heated under reflux for 4 hours with stirring. After cooling to the room temperature, 100 ml of water was added and the resultant mixture was extracted three times with each 110 ml of ether. The ether extract was successively washed with 110 ml of water, 150 g of 5% aqueous sodium thiosulfate solution and further twice with each 110 ml of water. The resulting ether solution was dried with anhydrous sodium sulfate, filtered, concentrated and distilled under vacuum to obtain 7.4 g (53.6 mM) of 4-ethylcatechol as a light yellow liquid having a boiling point of 111°-112° C./4 mmHg.

1. temperaturewas heated
2. temperatureunder reflux for 4 hours
3. additionwas added
4. extractionthe resultant mixture was extracted three times with each 110 ml of ether
5. extractionThe ether extract
6. washwas successively washed with 110 ml of water, 150 g of 5% aqueous sodium thiosulfate solution and further twice with each 110 ml of water
7. dry with materialThe resulting ether solution was dried with anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. distillationdistilled under vacuum

ORD record

ord-7df6feae15bd4fcca82836c07528b0d7

Source dataset

uspto-grants-1993_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05214034