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

HRID 611676Notes

Reaction equation

HRID 611676 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][CH2:16][C:17]([OH:19])=[O:18])=[CH:7][CH:6]=1)[CH2:2][CH3:3]>[Pd]>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Participants

3

Reactant 1

HCID 540395987-(p-Propoxyphenyl)-6-heptenoic acid

Product 1

HCID 187950747(p-Propoxyphenyl)heptanoic acidYield 93.1%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

This compound was synthesized from 7-(p-propoxyphenyl)-6-heptenoic acid (1.31 g, 5 mmol) by hydrogenation reaction using Pd/C (130 mg). Crystallization (petroleum ether) afforded the product (1.23 g, 93%) as white crystals (mp: 49-50° C.). IR: 3450-2550, 1725 cm-1 ; 1H-NMR: 1.00 (t, 3 H), 1.37 (m, 4 H), 1.60 (m, 4 H), 1.79 (m, 2 H), 2.36 (t, 2 H), 2.53 (t, 2 H), 3.87 (t, 2 H), 6.95 (q, 4 H), 9.80 (bs, 1 H). Anal. Calcd. for C16H24O3 : C, 72.69, H, 9.15%; Found: C, 72.79, H, 9.16%.

Workup

  1. customCrystallization (petroleum ether)

Sources & evidence

ORD record
ord-f48ce0d1bd4448189915beeb4c4797ea
Source dataset
uspto-grants-1999_12
Patent number
US06001869

Reaction notes

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