Water → 2-Butyl-3,5,5-trimethyl-2-cyclohexen-1-one

HRID 85337

Reaction equation

[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([CH3:10])=[CH:3]1.Br[CH2:12][CH2:13][CH2:14][CH3:15].[OH-].[K+].O>CN1CCCC1=O.C(OCC)(=O)C>[CH2:12]([C:3]1[C:2](=[O:1])[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4]=1[CH3:10])[CH2:13][CH2:14][CH3:15]

Participants

Conditions

Temperature: 70 °C

Procedure

In 60 ml of 1-methyl-2-pyrrolidone were dissolved 10.0 g (72.36 mmol) of isophorone and 14.9 g (95.6 mmol) of 1-bromobutane. To this mixture was added 8.1 g (144.4 mmol) of powdered potassium hydroxide and the mixture was stirred with heating at 70° C. for 6 hours. After the reaction mixture was added to water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residual liquid was purified by silica gel column chromatography to give 6.31 g of a yellow oily matter (yield: 44.9%).

Workup

washwashing with a saturated saline solution
dry with materialdrying over anhydrous sodium sulfate, and concentration
customThe residual liquid was purified by silica gel column chromatography
customto give 6.31 g of a yellow oily matter (yield: 44.9%)

Sources & evidence

ORD record: ord-99203777beb1432687e6cfaa2b21bd9b
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846955B2

Linked notes

Loading…