O-Cresol → HCID 12414461, compound

Participants

Reaction Steps

2-Hydroxybenzyl alcohol (18.6 g, 0.15 mol) and o-cresol (16.2 g, 0.15 mol) were dissolved in 150 ml of ether in a flask and a dry nitrogen atmosphere established. Ethyl magnesium bromide (100 ml of 3M solution in ether, 0.30 mol) was added dropwise with stirring. The ether was removed by evaporation under reduced pressure and 450 ml of benzene added. The resulting mixture was heated at reflux with stirring for 20 hours and then allowed to cool. Saturated aqueous ammonium chloride solution was added and the mixture extracted with 2-500 ml portions of ether. The combined ether extracts were dried over magnesium sulfate and the ether then removed by evaporation. The residue was chromatographed on a silica gel column eluting with an 80:20 mixture of hexane and ethyl acetate and dried in a vacuum oven at 100° C. to obtain 7.6 g (24 percent of theory) of (3-methyl-2-hydroxyphenyl) (2-hydroxyphenyl)methane as an oil.

Provenance & Evidence