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

HRID 1532533Notes

Reaction equation

HRID 1532533 reaction equation
[CH3:1]C([O-])(C)C.[K+].[CH2:7]([C:12]1([CH:29]=O)[CH2:17][CH2:16][CH:15]([CH:18]2[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:20][CH2:19]2)[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11].O>C1COCC1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:7]([C:12]1([CH:29]=[CH2:1])[CH2:17][CH2:16][CH:15]([CH:18]2[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:20][CH2:19]2)[CH2:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 962WaterHCID 154568234,4'-Dipentylbicyclohexyl-4-carbaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 154568244,4'-Dipentyl-4-vinylbicyclohexyl

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 17.84 g of KOtBu in 100 ml of THF is added dropwise at 0° C. 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-dd1f2c2214864d01a1d4d37b5855d06d
Source dataset
uspto-grants-2001_03
Patent number
US06203724B1

Reaction notes

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