1-Octanol → Octyl Acetate

HRID 1792248Notes

Reaction equation

[CH2:1]([OH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:10](OC=C)(=[O:12])[CH3:11].C(OCCCCCCCC)=C>C1(C)C=CC=CC=1>[C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:12])[CH3:11]

Participants

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 4MgCO3-Mg(OH)2-5H2O (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 18% and 3%, respectively, with a conversion from 1-octanol of 44%.

Workup

additionwere added

Sources & evidence

ORD record: ord-aa8ea40883fd4d5a90129da3c6e88bf3
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074970B2

Reaction notes

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