Water → 4,4'-Dipentyl-4-vinylbicyclohexyl

HRID 380253Notes

Reaction equation

HRID 380253 reaction equation
[CH3:1][C:2]([O-])([CH3:4])[CH3:3].[K+].O.[CH2:8]1[CH2:12]O[CH2:10][CH2:9]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:2]1([CH:4]=[CH2:4])[CH2:8][CH2:4][CH:2]([CH:1]2[CH2:12][CH2:12][CH:8]([CH2:9][CH2:10][CH2:1][CH2:2][CH3:3])[CH2:9][CH2:10]2)[CH2:3][CH2:3]1)[CH2:10][CH2:9][CH2:8][CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 154568244,4'-Dipentyl-4-vinylbicyclohexyl

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

A solution of 17.84 g of KOtBu in 100 ml of THF is added dropwise at 0C to a suspension of 53.20 g of 4,4,′-dipentylbicyclohexyl-4-carbaldehyde and 56.80 g of methyltriphenylphosphonium bromide in 300 ml of THF. The mixture is stirred at RT overnight, water is added, and the mixture is extracted with MTB ether. The combined organic phases are subjected to conventional work-up, giving 4,4′-dipentyl-4-vinylbicyclohexyl.

Workup

  1. extractionthe mixture is extracted with MTB ether

Sources & evidence

ORD record
ord-6cae63f338d6437ba0379063b5cd3385
Source dataset
uspto-grants-2001_10
Patent number
US06303194B1

Reaction notes

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