Benzaldehyde, 4-pentyl- → 6-(p-Pentylphenyl)-5-hexenoic acid

HRID 962973Notes

Reaction equation

HRID 962973 reaction equation
[CH2:1]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[Br-].[C:15]([CH2:18][CH2:19][CH2:20][CH2:21][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:17])=[O:16]>C1COCC1>[CH2:1]([C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[CH:21][CH2:20][CH2:19][CH2:18][C:15]([OH:17])=[O:16])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 23290Benzaldehyde, 4-pentyl-HCID 161236(4-Carboxybutyl)triphenylphosphonium bromide

Product 1

HCID 544444306-(p-Pentylphenyl)-5-hexenoic acidYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was synthesized from p-pentylbenzaldehyde (3.52 g, 20 mmol, prepared from p-pentylbenzoyl chloride and lithium tri(t-butoxy)aluminum hydride) and 4-carboxybutyltriphenylphosphonium bromide (8.86 g, 20 mmol) in THF (100 mL) by a Wittig reaction. Kugelrohr distillation (bp 147°-151° C./0.05 torr) afforded the product (2.49 g, 48%). IR: 3400-2500, 1725 cm-1 ; 1H-NMR: 0.90 (t, 3H), 1.28 (m, 6H), 1.82 (m, 2H), 1.37 (m, 4H), 2.57 (t, 2H), 5.55+6.10 (m, 1H), 6.38 (m, 1H), 7.10 (m, 4H), 10.50 (bs, 1H). Anal. Calcd. for C17H24O2 : C, 78.42, H, 9.29%; Found: C, 78.22, H, 9.27%. Z:E=35:65.

Workup

  1. distillationKugelrohr distillation (bp 147°-151° C./0.05 torr)

Sources & evidence

ORD record
ord-898ae852eae64944a50f40b8e4debfa8
Source dataset
uspto-grants-1998_06
Patent number
US05760259

Reaction notes

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