HCID 10910716, compound → 8Z-16-bromohexadec-8-enoic acid

HRID 1383272Notes

Reaction equation

HRID 1383272 reaction equation
[Br-].[C:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].[Br:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]=O>O1CCCC1>[Br:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]/[CH:39]=[CH:11]\[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3]

Participants

4

Reactant 2

HCID 10910716HCID 10910716, compoundHCID 11317723(7-Carboxyheptyl)triphenylphosphonium bromide

Product 1

HCID 867570938Z-16-bromohexadec-8-enoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

48.5 g (0.1 mol) of (7-carboxyheptyl)triphenylphosphonium bromide were suspended in 150 ml of tetrahydrofuran. After the addition of 24.7 g (0.22 mol) of potassium t-butylate in 50 ml of tetrahydrofuran 26.4 g (0.12 mol) of 8-bromooctanal were added dropwise. After the usual work up 35.4 g of crude 8Z-16-bromohexadec-8-enoic acid were obtained having the following characteristics: Z/E=93/6;

Workup

  1. additionwere added dropwise

Sources & evidence

ORD record
ord-421c2649b103421eb0e723514ee7b576
Source dataset
uspto-grants-2001_07
Patent number
US06255276B1

Reaction notes

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