Acetic Acid → 4-Propyl-1,2-benzenediol

A mixture of 15.0 g (83 mM) of 4-propylveratrole, 53.0 g (882 mM) of acetic acid and 159.4 g (926 mM of 47% hydrobromic acid was heated under reflux for 2 hours with stirring. After cooling to the room temperature, the reaction mixture was added with 140 ml of water and extracted three times with each 150 ml of ether. The extracted ether solution was successively washed with 150 ml of water, 150 g of 5% aqueous sodium thiosulfate solution and then twice with each 150 ml of water. The resulting solution was dried with anhydrous sodium sulfate, distilled off ether and vacuum distilled to obtain 10.5 g (69 mM) of 4-propylcatechol as a light yellow liquid having a boiling-point of 119° C./3 mmHg.

1. temperaturewas heated
2. temperatureunder reflux for 2 hours
3. extractionextracted three times with each 150 ml of ether
4. washThe extracted ether solution was successively washed with 150 ml of water, 150 g of 5% aqueous sodium thiosulfate solution
5. dry with materialThe resulting solution was dried with anhydrous sodium sulfate
6. distillationdistilled off ether and vacuum
7. distillationdistilled

ORD record

ord-f5b8da5fd16d4e23a7f8bb3414fa48ad

Source dataset

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04985458