Hydrochloric Acid → HCID 68796557, compound

Participants

Reaction Steps

To Mg (0.252 g, 10.4 mmol) in dry ether (5 mL) was added benzylbromide (1 mL, 8.41 mL) in dry ether (3 mL) dropwise under reflux. After the addition was complete, the reaction mixture was further refluxed for 1 h. Methyl 3,5-dimethoxy-4-i-propylbenzoate (1.00 g, 4.20 mmol) in ether (15 mL) was added. After the ester completely disappeared, the reaction mixture was cooled to room temperature. Water (10 mL) was added followed by addition of 2N HCl (10 mL) to dissolve precipitate. The organic layer was separated and the aqueous layer was extracted with ether (3×50 mL). The extract was dried over anhydrous Na2SO4. Evaporation of solvent followed by flash chromatography using ethyl acetate:hexane (1:9) afforded 2-(3,5-dimethoxy-4-i-propylphenyl)-1,3-diphenylpropan-2-ol (1.29 g, 79%) as a white solid. 1HNMR (CDCl3, ppm): δ 1.28 (d, J=7.2 Hz, 6H), 3.08 (d, J=13.3 Hz, 2H), 3.35 (d, J=13.3 Hz, 2H), 3.6 (m, 1H), 3.95 (s, 6H), 6.44 (s, 2H), 6.9-7.5 (m, 10H).

Provenance & Evidence