HCID 53992972, compound → HCID 18795083, compound

HRID 1004469Notes

Reaction equation

HRID 1004469 reaction equation
[CH2:1]([O:5][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][CH3:4]>[Pd]>[CH2:1]([O:5][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][CH3:4]

Participants

3

Reactant 1

HCID 53992972HCID 53992972, compound

Product 1

HCID 18795083HCID 18795083, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

This compound was synthesized from 6-(p-butoxyphenyl)-5-hexenoic acid (2.62 g, 10 mmol) by a hydrogenation reaction using Pd/C (260 mg). Crystallization (petroleum ether) afforded the product (2.49 g, 94%) as white crystals (mp 39-40° C.). IR: 3400=2500, 1705 cm-1 ; 1H-NMR: 0.96 (t, 3H), 1.35 (m, 2H), 1.50 (m, 2H), 1.62 (m, 4H), 1.75 (m, 2H), 2.35 (t, 2H), 2.52 (t, 2H), 3.92 (t, 2H), 6.95 (q, 4H), 10.30 (bs, 1H). Anal. Calcd. for C16H24O3 : C, 72.69, H, 9.15%; Found: C, 72.78, H, 9.18%.

Workup

  1. customCrystallization (petroleum ether)

Sources & evidence

ORD record
ord-e2f68d1f6d944dc0b16fe5af2611a259
Source dataset
uspto-grants-2000_04
Patent number
US06048989

Reaction notes

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