Oxalic Acid → HCID 23311350, compound

Participants

Reaction Steps

To a solution of 14.8 g (52 mmole) 4-dimethylamino-2-(2-hydroxyphenyl)-2-phenylbutanol in 300 ml CH2Cl2 and 21.5 ml (156 mmole) triethylamine which had been cooled in an ice bath for 20 minutes was added a solution of 6 ml (78 mmole) methanesulfonyl chloride in 50 ml CH2Cl2. After the mixture was stirred 3 hours at ice bath temperature, it was diluted with 800 ml CH2Cl2, washed with 10% NaOH solution (2×125 ml) and saturated NaCl solution (125 ml), and dried over MgSO4. Filtration and evaporation gave 14.0 g of a crude oil. A solution of 5 g of this material in 15 ml CH2Cl2 was added to excess oxalic acid in Et2O. The precipitated solid was recrystallized from ethanol to give 4.2 g (63%) of crystals, m.p. 158°-160°.

Provenance & Evidence