Diethyl Ether → 1-Dodecanol, 3,7,11-trimethyl-, (R*,R*)-

3.13 g (0.01157 mol) of 3(R),7(R),10-trimethyl-dodecanoic acid ethyl ester in dry ether (35 ml) was added dropwise to a mixture of lithium aluminum hydride (3.0 g) in 150 ml of dry diethyl ether. The mixture was refluxed with stirring for 21/2 hr. The flask was cooled in an ice-bath and the excess of lithium aluminum hydride was destroyed by carefully adding water, followed by 450 ml of 2 N H2SO4. The aqueous phase was extracted with diethyl ether (3×150 ml). The ether extract was washed with water (3×50 ml), saturated aqueous NaHCO3 (3×50 ml), water (3×50 ml) and dried over anhydrous magnesium sulfate. Evaporation of ether to dryness at reduced pressure yielded 2.70 g of crude material which on distillation (Kugelrohr oven, 104°-110°/0.10 mmHg) afforded 2.572 g (97.4%) of 3(R),7(R),11-trimethyl-dodecanol as a colorless oil.

1. temperatureThe mixture was refluxed
2. temperatureThe flask was cooled in an ice-bath
3. customthe excess of lithium aluminum hydride was destroyed by carefully adding water
4. extractionThe aqueous phase was extracted with diethyl ether (3×150 ml)
5. extractionThe ether extract
6. washwas washed with water (3×50 ml), saturated aqueous NaHCO3 (3×50 ml), water (3×50 ml)
7. dry with materialdried over anhydrous magnesium sulfate
8. customEvaporation of ether to dryness at reduced pressure
9. customyielded 2.70 g of crude material which
10. distillationon distillation (Kugelrohr oven, 104°-110°/0.10 mmHg)

ORD record

ord-daa7d5b9756b45bdbbd1acdd7d7fa84c

Source dataset

uspto-grants-1979_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04151360