3,5-Dimethylphenol → HCID 22479338, compound

Participants

Reaction Conditions

Reaction Steps

A reaction vessel was charged with methyl 2,2-dimethyl-3-tosyloxypropionate (Intermediate A7, 100 g, 0.35 mol), 3,5-dimethylphenol (45 g, 0.37 mol), potassium carbonate (73 g, 0.53 mol), and dimethylacetamide (300 mL). The mixture was heated on a steam bath for 16 hr and in a 170° C. bath for 6 hr. The cooled reaction mixture was diluted with 1 L water and extracted with 2×200 mL portions of ethyl acetate. The combined organic layers were washed with water, 0.5 M sodium hydroxide (twice), water, and saturated aqueous sodium chloride. The solvent was removed at aspirator pressure and high vacuum. The residue was taken up in dichloromethane and washed with several portions of 1 M sodium hydroxide, water, and saturated sodium chloride. The solution was concentrated, and the residue was distilled at 2 torr to yield 43.5 g (52%) of the title compound.

Provenance & Evidence