Propyltriphenylphosphonium bromide → HCID 10944737, compound

HRID 1106362Notes

Reaction equation

HRID 1106362 reaction equation
[CH:1]1([CH:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[Br-].[CH2:16]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:17][CH3:18].[CH3:38][C:39](C)([O-])[CH3:40].[K+]>C1COCC1>[CH:16](=[C:4]1[CH2:5][CH2:6][CH:1]([CH:8]2[CH2:13][CH2:12][C:11](=[CH:38][CH2:39][CH3:40])[CH2:10][CH2:9]2)[CH2:2][CH2:3]1)[CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 80374Propyltriphenylphosphonium bromideHCID 2648254,4'-BicyclohexanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 10944737HCID 10944737, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

29.1 g of bicyclohexyl-4,4'-dione and 123 g of propyl-triphenylphosphonium bromide were suspended in 300 ml of THF. The solution was cooled to 0° C., and a solution of 36 g of potassium tert-butoxide in 100 ml of THF was added dropwise, and the mixture was stirred at RT overnight. Conventional work-up gave 4,4'-dipropylidenebicyclohexyl.

Sources & evidence

ORD record
ord-9c4c92f60b49411b84dd57fec4538e32
Source dataset
uspto-grants-2000_05
Patent number
US06056895

Reaction notes

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