Potassium Carbonate → 3,5-Dihydroxybenzoic Acid

Participants

Reaction Steps

Ethyl-3,5-dihydroxybenzoate 1a (27.3 g, 150 mmol) was dissolved in acetone (750 mL). To this solution were added K2CO3 (20.7 g, 150 mmol) and 18-Crown-6 (1.9 g, 7.5 mmol) and stirred for 5 min. To this mixture, C8H17I (21.7 mL, 120 mmol) was added and stirred to reflux for 7 h. The reaction mixture was then cooled to room temperature and the solvent was evaporated to dryness. To this residue, water and ethyl acetate were added and stirred for 30 min. The organic layer was separated and aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine solution. The organic layer was evaporated to dry ness and purified by silica gel column chromatography (3-4% ethyl acetate in dichloromethane) to afford 14.5 g (33% yield) of 4. The major by-product of this reaction is the compound, where two octyl groups are added to the two phenolic groups of compound 1a. 1H NMR (400 MHz, CDCl3) δ 7.14 (s, 2H), 6.6 (t, J=2.2 Hz, 1H), 5.32 (s, 1H), 4.35 (q, J=7.2 Hz, 2H), 3.95 (t, J=6.6 Hz, 2H), 1.80-1.73 (quintet, 2H), 1.46-1.28 (m, 13H), 0.88 (t, J=6.8 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 166.8, 160.3, 156.8, 132.0, 109.0, 107.8, 106.9, 68.3, 61.3, 31.7, 29.3, 29.2, 29.1, 25.9, 22.6, 14.2, 14.0; GC/MS (m/z, r.i): 294 (M+, 68), 249 (12), 182 (100), 167 (8), 137 (25), 110 (12), 69 (12), 57 (8).

Provenance & Evidence