Oxalyl chloride → HCID 17816541, compound

Participants

Reaction Steps

In 10 ml of methylene chloride is dissolved 1.00 g of 3-(3-ethoxy-3-oxopropyl)-4-isobutoxybenzoic acid. After adding 0.36 ml of oxalyl chloride and 20 μl of N,N-dimethylformamide successively at ambient temperature, the mixture thus obtained is stirred at ambient temperature for one hour. Then, 0.95 g of aluminum chloride and 1.02 g of 1,3-diisopentyloxybenzene are successively added at 5-10° C., and stirred at the same temperature as above for 30 minutes and then at ambient temperature for 30 minutes. Then, 0.45 g of aluminum chloride is added at ambient temperature and stirred at the same temperature as above for 30 minutes. The reaction mixture is added to a mixture of methylene chloride and water, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue thus obtained is purified by silica gel column chromatography (eluent; hexane:ethyl acetate=10:1) to obtain 0.63 g of ethyl 3-[5-(2-hydroxy-4-isopentyloxybenzoyl)-2-isobutoxyphenyl]propanoate as a light yellow oily product. A 0.60 g portion of the oily product obtained above is dissolved in 12 ml of ethanol, 1.3 ml of 5 mol/L sodium hydroxide solution is added, and the mixture thus obtained is stirred at ambient temperature for 2 hours. Chloroform and water are added to the reaction mixture, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer thus obtained is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. Thus, 0.48 g of [5-(2-hydroxy-4-isopentyloxybenzoyl)-2-isobutoxyphenyl]-propanoic acid is obtained as a light yellow solid product.

Provenance & Evidence