12-Phenyl-10-dodecenoic acid → 12-Phenyllauric acid

HRID 1004471Notes

Reaction equation

HRID 1004471 reaction equation
[C:1]1([CH2:7][CH:8]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd]>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 5416015012-Phenyl-10-dodecenoic acid

Product 1

HCID 15192212-Phenyllauric acidYield 97.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

This compound was synthesized from 12-phenyl-10-dodecenoic acid (1.92 g, 7 mmol) by a hydrogenation reaction using Pd/C (190 mg). Crystallization (petroleum ether) afforded the product (1.88 g, 97%) as white crystals (mp 47-48° C.). IR: 3400-2500, 1700 cm-1 ; 1H-NMR: 1.30 (m, 14H), 1.60 (m, 4H), 2.32 (t, 2H), 2.57 (t, 2H), 7.20 (m, 5H), 10.20 (bs, 1H). Anal. Calcd. for C18H28O2 : C, 78.21, H, 10.21%; Found: C, 78.29, H, 10.25%.

Workup

  1. customCrystallization (petroleum ether)

Sources & evidence

ORD record
ord-7d9d6db63c0c4e27849239442572beb7
Source dataset
uspto-grants-2000_04
Patent number
US06048989

Reaction notes

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