Vinyl Acetate → 3,3-Dimethyl-1-vinyloxybutane

HRID 20331

Reaction equation

HRID 20331 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][OH:5].[C:8](OC=C)(=O)[CH3:9].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Ir].[Ir]>[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][O:5][CH:8]=[CH2:9]

Participants

6

Reactant 3

HCID 7904Vinyl AcetateHCID 10340Sodium CarbonateHCID 122333,3-Dimethyl-1-butanol

Product 1

HCID 663680153,3-Dimethyl-1-vinyloxybutane

Reagents, catalysts & solvents 2

HCID 6436381Chloro(1,5-cyclooctadiene)iridium(I) dimerCatalystHCID 241BenzeneSolvent

Procedure

Add chloro(1,5-cyclooctadiene)iridium(I) dimer (0.39 g, 0.59 mmol) to 3,3-dimethylbutan-1-ol (3.00 g, 29.35 mmol), vinyl acetate (10.11 g, 117.42 mmol) and sodium carbonate (1.87 g, 17.61 mmol) in benzene (10 mL) at room temperature. Boil under nitrogen 12 hours. Cool to room temperature and filter. Distill the filtrate and collect fraction boiling ˜125° C.-130° C. Flush through a silica gel pad with hexanes and concentrate to provide the title compound.

Workup

  1. custom12 hours
  2. filtrationfilter
  3. distillationDistill the filtrate
  4. customcollect fraction
  5. customboiling ˜125° C.-130° C
  6. customFlush through a silica gel pad with hexanes
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-226ce7882d634d20897871d2dacfff1a
Source dataset
uspto-grants-2010_06
Patent number
US07745438B2

Linked notes

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