1-Octanol → Octyl Acetate

HRID 1792244Notes

Reaction equation

HRID 1792244 reaction equation
F[B-](F)(F)F.C(=O)([O-])[O-].[Na+].[Na+].C(O)CCCCCCC.C(OC(C)=C)(=O)C.C(OCCCCCCCC)(C)=C.[CH2:40]([O:48][C:49]([O:52]CCCCCCCC)(C)[CH3:50])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]>C1(C)C=CC=CC=1>[C:49]([O:48][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])(=[O:52])[CH3:50]

Participants

8

Reactant 6

HCID 9571-OctanolHCID 7916Isopropenyl acetateHCID 10340Sodium CarbonateHCID 26255TetrafluoroborateHCID 141181512,2-Bis(1-octyloxy)propaneHCID 220345351-Octyl isopropenyl ether

Product 1

HCID 8164Octyl Acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of bis(1,5-cyclooctadiene)iridium tetrafluoroborate [Ir(cod)2]+BF4− (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 67%, 6%, and 14%, respectively, with a conversion from 1-octanol of 93%.

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-bb0ae9e5c0614e48b91c03afdb979d47
Source dataset
uspto-grants-2006_07
Patent number
US07074970B2

Reaction notes

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