Hydrochloric Acid → 3-Methyl-6-hydroxybenzofuran
Reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][C:7](=O)[CH3:8].[OH-].[K+].Cl>>[CH3:8][C:7]1[C:10]2[CH:11]=[CH:12][C:2]([OH:1])=[CH:3][C:4]=2[O:5][CH:6]=1Participants
4
Conditions
- Temperature
- 5 °C
Procedure
3 g (18 mmol) of (3-hydroxyphenoxy)acetone and 400 ml of a 0.1M potassium hydroxide solution are introduced into a 1 l three-necked flask equipped with a reflux condenser. Heating is carried out at reflux for 6 hours. The reaction mixture is cooled to 5° C., a molar hydrochloric acid solution is added, in order to obtain a pH of approximately 5, and extraction is carried out with ethyl ether (3×150 ml). The organic phases are combined, dried over magnesium sulphate and concentrated. The residue is purified by silica column chromatography (elution solvent: 8/2 cyclohexane/ethyl acetate). 1.61 g of 3-methyl-6-hydroxybenzofuran are obtained--M.p.: 92° C.