10-bromodecanal → HCID 88227136, compound

HRID 1383289Notes

Reaction equation

HRID 1383289 reaction equation
[Br-].[C:2]([CH2:5][CH:6]([CH3:28])[CH2:7][CH2:8][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>C1COCC1>[CH3:28][CH:6]([CH2:7]/[CH:8]=[CH:39]\[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][Br:29])[CH2:5][C:2]([OH:4])=[O:3]

Participants

4

Reactant 2

HCID 1093343910-bromodecanalHCID 18348366HCID 18348366, compound

Product 1

HCID 88227136HCID 88227136, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

68.1 g (149 mmol) of (4-carboxy-3-methyl-butyl)-triphenylphosphonium bromide were placed in 150 ml of THF and treated with 33.4 g (298 mmol) of potassium t-butylate in 50 ml of THF. 35 g (149 mmol) of 10-bromodecanal were added to this mixture After usual work up 111.8 g of crude product were obtained and, after chromatography, 29 g of 3-methyl-5Z-15-bromopentadec-5-enoic acid were obtained having the following characteristics:

Workup

  1. customwere obtained

Sources & evidence

ORD record
ord-9cb257bc81aa43f6858849b0bbdcf4ce
Source dataset
uspto-grants-2001_07
Patent number
US06255276B1

Reaction notes

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