Dimethyl Sulfate → 5-Methoxy-4-methyl-3-decene

Temperature

80 °C

5.0 g of 4-methyl-3-decen-5-ol dissolved in 25 ml of toluene are added dropwise over a period of 30 minutes at 80° C. while stirring to 1.54 g of a 55-60% sodium hydride dispersion in 25 ml of toluene. The mixture is stirred at 80° C. for 12 hours, cooled to 40° C. and treated dropwise with 5.6 g of dimethyl sulphate, the temperature again rising to 80° C. In order to complete the reaction, the mixture is stirred at 80° C. for a further 3 hours. After cooling to 40° C., 10 ml of ethanol are added thereto. The mixture is heated to boiling for a short period and then treated with cold 2N sodium hydroxide. The product is taken up in hexane, washed neutral, chromatographed on 250 g of silica gel in order to remove the oil of the sodium hydride dispersion used and the thus-obtained crude product is fractionally distilled. There are obtained 4.1 g (76% of theory) of 5-methoxy-4 -methyl-3-decene of boiling point 100°-105° C./14 Torr, nD20 =1.4337. Odour: very fresh, fruity, green, apple-like, blueberries, blackberries, herbaceous.

1. additionare added dropwise over a period of 30 minutes at 80° C.
2. temperaturecooled to 40° C.
3. customagain rising to 80° C
4. customthe reaction
5. stirringthe mixture is stirred at 80° C. for a further 3 hours
6. temperatureAfter cooling to 40° C.
7. temperatureThe mixture is heated
8. waitto boiling for a short period
9. washwashed neutral
10. customchromatographed on 250 g of silica gel in order
11. customto remove the oil of the sodium hydride dispersion
12. customthe thus-obtained crude product
13. distillationis fractionally distilled

ORD record

ord-f6bb9eb709d4429f9c86ce8b47f9a304

Source dataset

uspto-grants-1990_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04948781