Vinyl Acetate → 6-(Ethenyloxy)-1-hexanol

HRID 1792240Notes

Reaction equation

HRID 1792240 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C(O)CCCCCO.C(OC=C)(=O)C.[CH:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][O:30]C=C)=[CH2:22]>C1(C)C=CC=CC=1>[CH:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][OH:30])=[CH2:22]

Participants

6

Reactant 4

HCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 123741,6-HexanediolHCID 882291,6-Bis(vinyloxy)hexane

Product 1

HCID 220261996-(Ethenyloxy)-1-hexanol

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 (6.7 mg, 0.01 mmol) and sodium carbonate (64 mg, 0.6 mmol) in toluene (1.0 ml), 1,6-hexanediol (118 mg, 1 mmol) and vinyl acetate (344 mg, 4 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 6 hours. The reaction mixture was analyzed by gas chromatography to find that 1,6-bis(vinyloxy)hexane and 6-vinyloxy-1-hexanol were produced in yields of 87% and 2%, respectively, with a conversion from 1,6-hexanediol of 97%.

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-385a60180831478591c2e7f190c4b233
Source dataset
uspto-grants-2006_07
Patent number
US07074970B2

Reaction notes

Loading…