Dimethyl Pentadecanedioate → Methyl 15-Hydroxypentadecanoate

HRID 2299574

Reaction equation

HRID 2299574 reaction equation
[C:1](OC)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16].[H][H]>[Cr].[Cu]>[OH:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 11415366Dimethyl PentadecanedioateHCID 178418361HCID 178418361, compound

Product 1

HCID 3496889Methyl 15-HydroxypentadecanoateYield 35%

Reagents, catalysts & solvents 1

HCID 9833946Chromium, compd. with copper (1:1)Catalyst

Procedure

150 g (499 mmol) of dimethyl 1,15-pentadecandioate and 750 mg (0.5% by weight per the diester) of a commercial copper-chromium catalyst (content of copper as copper oxides: 42% by weight) were added to an autoclave and subjected to hydrogenation reaction at the hydrogen pressure of 20.0 Mpa at 280° C. After 2 hours, methyl 15-hydroxypentadecanoate was obtained in 35% yield. The degree of the conversion was 67% the selectivity was 53%, and the yield was 35%.

Sources & evidence

ORD record
ord-a9ac413624b5490cabdb2384afb428f9
Source dataset
uspto-grants-2002_12
Patent number
US06495706B2

Linked notes

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