Vinyl Acetate → HCID 22034522, compound

HRID 916907Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[C:7]12([OH:17])[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2.[C:18]([O:21][CH:22]=[CH2:23])(=[O:20])[CH3:19].C(OC12CC3CC(CC(C3)C1)C2)=C>C1(C)C=CC=CC=1>[C:18]([O:21][CH:22]([O:17][C:7]12[CH2:14][CH:13]3[CH2:12][CH:11]([CH2:10][CH:9]([CH2:15]3)[CH2:8]1)[CH2:16]2)[CH3:23])(=[O:20])[CH3:19]

Participants

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-adamantanol (152 mg, 1 mmol) and vinyl acetate (258 mg, 3 mmol) were added, followed by stirring at 100° C. in an atmosphere of argon gas for 5 hours. The reaction mixture was analyzed by gas chromatography to find that 1-adamantyl vinyl ether and 1-(adamant-1-yloxy)ethyl acetate were produced in yields of 91% and 1%, respectively, with a conversion from 1-adamantanol of 93%.

Workup

additionwere added

Sources & evidence

ORD record: ord-fd36982aad99469f98d85a40fa3990a6
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271297B2

Reaction notes

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