1-Octanol → Octyl Acetate

HRID 916913

Reaction equation

HRID 916913 reaction equation
C(=O)([O-])O.[Na+].[CH2:6]([OH:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[C:15](OC=C)(=[O:17])[CH3:16].C(OCCCCCCCC)=C>C1(C)C=CC=CC=1>[C:15]([O:14][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])(=[O:17])[CH3:16]

Participants

6

Reactant 4

HCID 9571-OctanolHCID 7904Vinyl AcetateHCID 702491-(Vinyloxy)octaneHCID 516892Sodium Bicarbonate

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 sodium hydrogencarbonate (1.2 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 93% and 2%, respectively, with a conversion from 1-octanol of 99%.

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-a4c5619489ae4d0ca109aece78aadc77
Source dataset
uspto-grants-2007_09
Patent number
US07271297B2

Linked notes

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