Sodium Hydroxide → 5-Undecen-4-one, 7-ethyl-2-methyl-

HRID 1596038Notes

Reaction equation

HRID 1596038 reaction equation
[CH2:1]([CH:3]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:4][CH2:5][CH:6]([OH:11])[CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:2].C(C(CCCC)C=O)C.[OH-].[Na+]>C(C(C)=O)C(C)C>[CH2:1]([CH:3]([CH2:12][CH2:13][CH2:14][CH3:15])[CH:4]=[CH:5][C:6](=[O:11])[CH2:7][CH:8]([CH3:10])[CH3:9])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312412-EthylhexanalHCID 979484-Undecanol, 7-ethyl-2-methyl-

Product 1

HCID 735570515-Undecen-4-one, 7-ethyl-2-methyl-

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

In particular, the process of the invention is suitable for preparing 7-ethyl-2-methyl-4-undecanol (tetradecanol) by aldol condensation of methyl isobutyl ketone and 2-ethylhexanal at 90-110° C. in the presence of a 40-50% strength aqueous sodium hydroxide solution to form 7-ethyl-2-methylundec-5-en-4-one with subsequent hydrogenation to give the above-mentioned alcohol. The hydrogenation catalyst used here is, preferably, a nickel catalyst supported on kieselguhr.

Sources & evidence

ORD record
ord-c70cf4e6d8ca4f3a9aa7f3b26b38ddd8
Source dataset
uspto-grants-2001_09
Patent number
US06288288B1

Reaction notes

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