6-(p-Propoxyphenyl)-5-hexenoic acid → 6-(p-Propoxyphenyl)hexanoic acid

HRID 962963Notes

Reaction equation

HRID 962963 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[CH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:7][CH:6]=1)[CH2:2][CH3:3]>[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

3

Reactant 1

HCID 540403946-(p-Propoxyphenyl)-5-hexenoic acid

Product 1

HCID 158876376-(p-Propoxyphenyl)hexanoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 16218511Pd barium sulfateCatalyst

Procedure

This compound was synthesized from 6-(p-propoxyphenyl)-5-hexenoic acid (1.49 g, 6 mmol) and Pd/BaSO4 (150 mg) by a hydrogenation reaction. Crystallization (petroleum ether) yielded the product (1.38 g, 92%) as white crystals (mp 42°-43° C.), IR: 3400-2500, 1715 cm-1 ; 1H-NMR: 1.00 (t, 3H), 1.55 (m, 8H), 2.40 (m, 4H), 3.90 (t, 2H), 6.95 (q, 4H), 7.90 (bs, 1H). Anal. Calcd. for C15H22 O3 : C, 71.97, H, 8.86%; Found: C, 72.04, H, 8.88%.

Workup

  1. customCrystallization (petroleum ether)

Sources & evidence

ORD record
ord-decca2e05b7246759c69efc67c0b3a08
Source dataset
uspto-grants-1998_06
Patent number
US05760259

Reaction notes

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