1-Octanol → 1-(1-Octyloxy)ethyl acetate

HRID 916912

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([OH:15])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:16]([O:19][CH:20]=[CH2:21])(=[O:18])[CH3:17].C(OCCCCCCCC)=C.C(OCCCCCCCC)(=O)C>C1(C)C=CC=CC=1>[C:16]([O:19][CH:20]([O:15][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH3:21])(=[O:18])[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of di-1-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (0.01 mmol) and sodium carbonate (0.1 mmol) in toluene (1.0 ml), 1-octanol (130 mg, 1 mmol) and vinyl acetate (5 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, octyl acetate, and 1-(1-octyloxy)ethyl acetate were produced in yields of 58%, 3%, and 21%, respectively, with a conversion from 1-octanol of 100%.

Workup

additionwere added

Sources & evidence

ORD record: ord-9ae999423ea0441593e4508c7b2c6acf
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271297B2

Linked notes

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