alpha-Hydroxyacetophenone → Monomethyl terephthalate

Participants

Reaction Steps

To a solution of the thus-obtained 112 mg of 2-hydroxyacetophenone in 10 ml of pyridine was added 300 mg of terephthalic acid monomethyl ester chloride and the mixture stirred at room temperature for one night. The reaction mixture was diluted with ethyl acetate and washed with water, Cu(NO3) 0.2aq, water, sodium bicarbonate solution, saturated saline solution and dried over MgSO4. The distillation of the solvent and purification by chromatography through silica gel column gave 161 mg (yield: 82.8%) of the derivative of terephthalic acid methylester. To a solution of 257 mg of the thus-obtained methylester in 5 ml of pyridine was added 75 mg of caustic potash and the mixture stirred at room temperature for one night. The reaction mixture was poured over 20 ml of 20% acetic acid and extracted in ethyl acetate. The resulting organic layer was washed with water 2-3 times and dried over MgSO4. The distillation of the solvent and purification by chromatography through silica gel column gave 135 mg (yield: 62.8%) of the rearranged product (IV, R1, R2 =(CH3)2CCH2CH2O, R3 =CH3, as orange needles having a melting point of 193°-195.5° C. (CH2Cl2 -hexane).

Provenance & Evidence