1-Octanol → Octyl Acetate

HRID 916910Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].C(O)CCCCCCC.C(OC(C)=C)(=O)C.C(OCCCCCCCC)(C)=C.[CH2:35]([O:43][C:44]([O:47]CCCCCCCC)(C)[CH3:45])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42]>C1(C)C=CC=CC=1>[C:44]([O:43][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])(=[O:47])[CH3:45]

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 sodium carbonate (0.03 mmol) in toluene (1.0 ml), 1-octanol (130 mg, 1 mmol) and isopropenyl acetate (5 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 15 hours. The reaction mixture was analyzed by gas chromatography to find that 1-octyl isopropenyl ether, 2,2-bis(1-octyloxy)propane, and octyl acetate were produced in yields of 78%, 4%, and 16%, respectively, with a conversion from 1-octanol of 98%.

Workup

additionwere added

Sources & evidence

ORD record: ord-13c09113c36b4499a82fe02631cf25da
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271297B2

Reaction notes

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