1-Octanol → Octyl Acetate

HRID 916916

Reaction equation

HRID 916916 reaction equation
C(N(CC)CC)C.[CH2:8]([OH:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[C:17](OC=C)(=[O:19])[CH3:18].C(OCCCCCCCC)=C>C1(C)C=CC=CC=1>[C:17]([O:16][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(=[O:19])[CH3:18]

Participants

6

Reactant 4

HCID 9571-OctanolHCID 7904Vinyl AcetateHCID 8471TriethylamineHCID 702491-(Vinyloxy)octane

Product 1

HCID 8164Octyl Acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (0.01 mmol) and triethylamine (0.6 mmol) in toluene (1.0 ml), 1-octanol (130 mg, 1 mmol) and vinyl acetate (2 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 2 hours. The reaction mixture was analyzed by gas chromatography to find that 1-octyl vinyl ether and octyl acetate were produced in yields of 19% and 2%, respectively, with a conversion from 1-octanol of 30%.

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-ea4eeb819e2e445d8232e0fb14f9e1e0
Source dataset
uspto-grants-2007_09
Patent number
US07271297B2

Linked notes

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