7-(p-Ethoxyphenyl)-6-heptenoic acid → 7-(p-Ethoxyphenyl)heptanoic acid

HRID 610683Notes

Reaction equation

HRID 610683 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:6][CH:5]=1)[CH3:2]>[Pd]>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:6][CH:5]=1)[CH3:2]

Participants

3

Reactant 1

HCID 539540487-(p-Ethoxyphenyl)-6-heptenoic acid

Product 1

HCID 187950767-(p-Ethoxyphenyl)heptanoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

This compound was synthesized from 7-(p-ethoxyphenyl)-6-heptenoic acid (1.24 g, 5 mmol) and Pd/C (125 mg) by a hydrogenation reaction. Crystallization (petroleum ether) afforded the product (1.21 g, 97%) as white crystals (mp 65-66° C). IR: 3400-2500, 1715 cm-1 ; 1H-NMR: 1.32 (m, 7H), 1.55 (m, 5H), 2.30 (t, 2H), 2.50 (t, 2H), 3.95 (q, 2H), 6.90 (q, 2H), 10.20 (bs, 1H). Anal. Calcd. for C15H22O3 : C, 71.97, H, 8.86%; Found: C, 71.91, H, 8.87%.

Workup

  1. customCrystallization (petroleum ether)

Sources & evidence

ORD record
ord-ac14160f763b46d28860baa525a05339
Source dataset
uspto-grants-1999_12
Patent number
US05998642

Reaction notes

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