4-Propylcyclohexanone → 4-[2-(4-Propylcyclohexylidene)ethyl]propylidenecyclohexane

HRID 1106366Notes

Reaction equation

[CH2:1]([CH:4]1[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:19][CH2:20][CH:21]2[CH2:26][CH2:25][C:24](=[CH:27][CH2:28][CH3:29])[CH2:23][CH2:22]2)C=CC=CC=1.CC(C)([O-])C.[K+]>C1COCC1>[CH2:1]([CH:4]1[CH2:9][CH2:8][C:7](=[CH:19][CH2:20][CH:21]2[CH2:22][CH2:23][C:24](=[CH:27][CH2:28][CH3:29])[CH2:25][CH2:26]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: -10 °C

Procedure

57.0 g of 4-propylcyclohexanone and 25.0 g of triphenyl[2-(4-propylidenecyclohexyl)ethyl]phosphonium bromide were introduced into 150 ml of THF under nitrogen, and the mixture was cooled to -10° C. A solution of 5.61 g of potassium tert-butoxide in 100 ml of THF was then added dropwise with stirring, and the mixture was stirred at RT for a further 2 h. Conventional work-up gave 4-[2-(4-propylcyclohexylidene)ethyl]propylidenecyclohexane.

Workup

stirringthe mixture was stirred at RT for a further 2 h

Sources & evidence

ORD record: ord-9f5a8e42bd594fb3be18f9f2ef963672
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06056895

Reaction notes

Loading…