Methanol → HCID 54205995, compound

Participants

Reaction Steps

9.42 g (51 mmol) of methyl (R)-(+)-citronellate (9) are dissolved in 26 ml of methanol and saturated with 2.45 g (51 mmol) of 03 for 1 h at -30° C. Then 3.12 g (82 mmol) of NaBH4 (sic) are added in small portions with stirring. During the highly exothermic reaction, which lasts for 2 h, the temperature is kept between -20° C. and +10° C. Then cooling is discontinued and the mixture is brought to room temperature. A high proportion of the methanol is distilled off and to the residue are added 80 ml of CHCl3. This mixture is added at 0° C. to a vigorously stirred solution of 50 ml of conc. HCl in 100 g of ice. The chloroform phase is washed once with Na2CO3 solution and three times with H2O and is then dried over MgSO4 and concentrated. The crude product is distilled through a bulb tube.

Provenance & Evidence