Methanol → HCID 54205995, compound

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.

1. customDuring the highly exothermic reaction, which
2. customis kept between -20° C. and +10° C
3. temperatureThen cooling
4. customis brought to room temperature
5. distillationA high proportion of the methanol is distilled off and to the residue
6. additionare added 80 ml of CHCl3
7. additionThis mixture is added at 0° C. to a vigorously stirred solution of 50 ml of conc. HCl in 100 g of ice
8. washThe chloroform phase is washed once with Na2CO3 solution and three times with H2O
9. dry with materialis then dried over MgSO4
10. concentrationconcentrated
11. distillationThe crude product is distilled through a bulb tube

ORD record

ord-6d0395be92f646e68a6148560276dc5f

Source dataset

uspto-grants-1993_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05227090