Lithium hydride → 8-Nonen-2-one

Temperature

0 °C

To a stirred mixture of 11.0 g lithium hydride in 800 ml of anhydrous ether, there was added dropwise 164 g of oct-7-enoic acid (prepared in Example 22 B-2) in 800 ml of anhydrous ether and the mixture was cooled to 0° C. and 650 ml of 2 M methyllithium in ether was added dropwise and then allowed to warm to room temperature and stir for 4.5 hr. This mixture was quenched by pouring the slurry into rapidly stirred 10% aqueous hydrochloric acid (1.2 liter) and wet ice. The resulting mixture was extracted with ether (3×700 ml). The continued ether extracts were washed with 10% aqueous sodium hydroxide and then with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo to yield 118.9 g of the title compound having the following physical characteristics:

1. temperatureto warm to room temperature
2. customThis mixture was quenched
3. additionby pouring the slurry into rapidly stirred 10% aqueous hydrochloric acid (1.2 liter) and wet ice
4. extractionThe resulting mixture was extracted with ether (3×700 ml)
5. washThe continued ether extracts were washed with 10% aqueous sodium hydroxide
6. dry with materialwith saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate
7. customThe solvent was removed in vacuo

ORD record

ord-fabc2d92b88c4c309ad679b15dea51ab

Source dataset

uspto-grants-1980_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04220795