Hydrochloric Acid → HCID 18790055, compound

Participants

Reaction Steps

To a solution of 5-phenylvaleric acid (10 g, 56.1 mmol) in dichloromethane (70 mL) is added 2 M oxalyl chloride (33.5 mL, 67 mmol). The mixture is stirred at room temperature for 18 hours. The solvent is removed in vacuo. The residue is dissolved in dichloromethane (60 mL) and veratrole (11.6 g, 84 mmol) is added. The mixture is cooled in ice and aluminum chloride (7.4 g, 56.1 mmol) is added in portions over 10 minutes. The mixture is stirred for 3 hours warming to room temperature. The mixture is added to aqueous HCl and is extracted with dichloromethane. The organic layer is washed with water and is dried over MgSO4. The solvent is removed in vacuo and the residue is chromatographed on silica gel (7:3 hexane:ethyl acetate) to give 1-(3,4-dimethoxyphenyl)-1-oxo-5-phenylpentane (5.5 g 33%), m.p. 56-8° C. 1H-NMR (300 MHz, CDCl3) δ (TMS) 1.68-1.82 (m, 4H), 2.52-2.61 (t, 2H), 2.88-2.98 (t, 2H), 3.95 (s, 6H), 6.82-6.92 (m, 2H), 7.10-7.30 (m, 4H), 7.48-7.60 (m, 2H); MS (EI) m/e 298 (M+).

Provenance & Evidence