1-Octanol → Octyl Acetate

HRID 916917Notes

Reaction equation

HRID 916917 reaction equation
F[B-](F)(F)F.C(=O)([O-])[O-].[Na+].[Na+].[CH2:12]([OH:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[C:21](OC=C)(=[O:23])[CH3:22].C(OCCCCCCCC)=C>C1(C)C=CC=CC=1>[C:21]([O:20][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])(=[O:23])[CH3:22]

Participants

7

Reactant 5

HCID 9571-OctanolHCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 26255TetrafluoroborateHCID 702491-(Vinyloxy)octane

Product 1

HCID 8164Octyl Acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of (1,5-cyclooctadiene)(acetonitrile)iridium tetrafluoroborate [Ir(cod)(CH3CN)]+BF4− (0.01 mmol) and sodium carbonate (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 90% and 1%, respectively, with a conversion from 1-octanol of 98%.

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-2b894077752b4c84af78b862e66a469f
Source dataset
uspto-grants-2007_09
Patent number
US07271297B2

Reaction notes

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