Hydrochloric Acid → Methyl 3-(3,4-dimethylphenyl)-3-oxopropanoate

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Reaction Steps

To a stirring solution of 3,4-dimethylacetophenone (1.0 g, 6.8 mmol) in tetrahydrofuran (10 ML) at 0° C. under an atmosphere of nitrogen was added potassium hexamethyldisilylzide (1.46 g, 6.8 mmol). Resulting suspension was stirred for 10 min and dimethylcarbonate (0.58 mL, 6.8 mmol) added. Reaction stirred for 16 h warming to room temperature then poured onto wet ice (50 mL)/ hydrochloric acid (5 mL). Product extracted with ethyl acetate (50 mL) and organic washed with saturated sodium chloride then dried over magnesium sulfate. Product isolated as an amber oil after removal of solvent under vacuum. M+1=207.

Provenance & Evidence