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

HRID 377484Notes

Reaction equation

HRID 377484 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]>[Pd]>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

3

Reactant 1

HCID 544444306-(p-Pentylphenyl)-5-hexenoic acid

Product 1

HCID 187950846-(p-Pentylphenyl)hexanoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

This compound was synthesized from 6-(p-pentylphenyl)-5-hexenoic acid (1.30 g, 5 mmol) by hydrogenation reaction using Pd/C (130 mg). Crystallization (petroleum ether) afforded the product (1.13 g, 87%) as white crystals (mp 29-30° C.), IR: 3400-2500, 1730 cm-1 ; 1H-NMR: 0.89 (t, 3H), 1.32 (m, 6H), 1.60 (m, 6H), 2.35 (t, 2H), 2.58 (m, 4H), 7.07 (s, 1H), 10.30 (bs, 1H). Anal. Calcd. for C17H26O2 : C, 77.82, H, 9.99%; Found: C, 77.56, H, 9.90%.

Workup

  1. customCrystallization (petroleum ether)

Sources & evidence

ORD record
ord-138b2dff46ed4a58bc039d9c42d1e811
Source dataset
uspto-grants-2000_02
Patent number
US06025511

Reaction notes

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