Triethylamine → Oct-2-enyl acetate

HRID 892635

Reaction equation

HRID 892635 reaction equation
[C:1]([O:4][CH2:5][CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][CH:11]=[CH2:12])(=[O:3])[CH3:2].C(N(CC)CC)C>C(O)C>[C:1]([O:4][CH2:5][CH:6]=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:3])[CH3:2].[C:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 190132,7-Octadien-1-ol, 1-acetate

Product 2

HCID 8164Octyl AcetateYield 23.6%HCID 102248Oct-2-enyl acetateYield 63.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 33.6 grams of 1-acetoxyocta-2,7-diene (I), 0.30 g RuCl2 (PPh3)3, 1.5 ml triethylamine and 120 ml ethanol was heated in a 300 ml stainless steel autoclave under a hydrogen pressure of 450 psi at 30° C. After three hours the rate of hydrogenation was greatly decreased and the pressure drop corresponded to approximately the theoretical amount (0.2 moles). The reaction was stopped, the catalyst filtered off and the crude product analyzed by GC to give 12.5% I, 63.7% 1-acetoxyoct-2-ene (II), and 23.6% 1-acetoxyoctane (III). This corresponds to a selectivity of 72.8% for the formation of II at a 87.5% conversion of I.

Workup

  1. filtrationthe catalyst filtered off

Sources & evidence

ORD record
ord-10021cf70af14a6da6cba3c07fc5e37f
Source dataset
uspto-grants-1992_06
Patent number
US05118837

Linked notes

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