Vinyl Acetate → 1,3-Bis(1-methyl-1-vinyloxyethyl)benzene

HRID 2111052Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[C:7](OC=C)(=O)[CH3:8].[OH:13][C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([CH3:28])([O:25][CH:26]=[CH2:27])[CH3:24])[CH:18]=1)([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[CH3:24][C:23]([C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:14]([O:13][CH:7]=[CH2:8])([CH3:16])[CH3:15])[CH:18]=1)([O:25][CH:26]=[CH2:27])[CH3:28]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) [Ir(cod)Cl]2 (67 mg, 0.1 mmol) and sodium carbonate (640 mg, 6 mmol) in toluene (5 ml) were added α,α, α′, α′-tetramethyl-1,3-benzenedimethanol (5 mmol) and vinyl acetate (2.15 g, 25 mmol), 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-(1-hydroxy-1-methylethyl)-3-(1-methyl-1-vinyloxyethyl)benzene and 1,3-bis(1-methyl-1-vinyloxyethyl)benzene were formed in yields of 8% and 70%, respectively, with a conversion from α,α,α′, α′-tetramethyl-1,3-benzenedimethanol of 98%.

Workup

additionwere added α,α

Sources & evidence

ORD record: ord-fb4a950a0f14478bbc2151eb1ced739a
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07518021B2

Reaction notes

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