Protocatechuic Acid → Propyl 3,4-dipropoxybenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3,4-dihydroxybenzoic acid (0.65 g; 4.22 mmol), anhydrous K2CO3 (1.75 g; 12.7 mmol) and n-PrBr (1.5 ml; 4 mmol) in anhydrous DMF (5 ml) was stirred at ˜55° C. overnight. After cooling to room temperature, the mixture was diluted to 25 ml with EtOAc, washed with H2O (2×10 ml), brine, dried over anhydrous MgSO4, filtered and the filtrate evaporated to dryness to give the title compound (0.94 g; 80%), as heavy syrup, which was used in next step without further purification. 1H-NMR (CDCl3) 0.97-1.04 (m, 9H); 1.7-1.9 (m, 6H); 3.97-4.02 (m, 4H); 4.2-4.26 (m, 2H); 6.85 (d, 1H, J=8.4 Hz); 7.53 (s, 1H); 7.62 (d, 1H, J=8.4 Hz).

Provenance & Evidence