4-Butylbenzaldehyde → 7-(p-Butylphenyl)-6-heptenoic acid

HRID 610693Notes

Reaction equation

HRID 610693 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].[CH2:29]([C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1)[CH2:30][CH2:31][CH3:32]>C1COCC1>[CH2:29]([C:33]1[CH:40]=[CH:39][C:36]([CH:37]=[CH:9][CH2:8][CH2:7][CH2:6][CH2:5][C:2]([OH:4])=[O:3])=[CH:35][CH:34]=1)[CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 709884-ButylbenzaldehydeHCID 2779280(5-Carboxypentyl)triphenylphosphanium bromide

Product 1

HCID 540049817-(p-Butylphenyl)-6-heptenoic acidYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was synthesized from 5-carboxypentyltriphenylphosphonium bromide (9.50 g, 20 mmol) and p-butylbenzaldehyde (3.24 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Kugelrohr distillation yielded the product (2.67 g, 51%) as a colorless oil (bp 154-157° C./0.05 torr). IR: 3400-2500, 1720 cm-1, 1H-NMR:0.92 (t, 3H), 1.50 (m, 8H), 2.30 (m, 4H), 2.58 (m, 2H), 5.58+6.15 (m, 1H), 6.38 (t, 1H), 7.18 (m, 4H), 10.30 (bs, 1H). Anal. Calcd. for C17H24O2 : C, 78.42, H, 9.29%: Found: C, 78.38, H, 9.29%. Z:E=62:38.

Workup

  1. distillationKugelrohr distillation

Sources & evidence

ORD record
ord-a4a724adb8144653947b3367b4c12b50
Source dataset
uspto-grants-1999_12
Patent number
US05998642

Reaction notes

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