(5-Carboxypentyl)triphenylphosphanium bromide → HCID 86757096, compound

HRID 1383279Notes

Reaction equation

HRID 1383279 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[Br:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=O>O1CCCC1>[Br:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]/[CH:39]=[CH:9]\[CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3]

Participants

4

Reactant 2

HCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideHCID 1093343910-bromodecanal

Product 1

HCID 86757096HCID 86757096, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

60 g (0.13 mol) of (5-carboxypentyl)triphenylphosphonium bromide were suspended in 250 ml of tetrahydrofuran. 30 g (0.26 mol) of potassium t-butylate in 20 ml of tetrahydrofuran were then added. Subsequently, 26 g (0/11 mol) of 10-bromodecanal were added. After usual work up 28 g (65%) of crude 6Z-16-bromohexadec-6-enoic acid were obtained having the following characteristics: Z/E=93/7;

Sources & evidence

ORD record
ord-45b3a100f5c04085a552849f4fcc1e60
Source dataset
uspto-grants-2001_07
Patent number
US06255276B1

Reaction notes

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