Vinyl Acetate → HCID 54044222, compound

HRID 745966Notes

Reaction equation

HRID 745966 reaction equation
[CH3:1][O:2][C:3]([CH3:8])([CH3:7])[C:4]([OH:6])=[O:5].[OH-].[K+].[OH-].[Na+].[C:13](OC=C)(=O)[CH3:14]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:13]([O:5][C:4](=[O:6])[C:3]([O:2][CH3:1])([CH3:8])[CH3:7])=[CH2:14]

Participants

6

Procedure

A mixture of 2-methoxy-2-methylpropanoic acid (5.9 g), vinyl acetate (5 ml), mercuric acetate (172 mg), palladium acetate (27 mg) and potassium hydroxide (225 mg) was stirred under nitrogen at ca 50° for 4 hours. More vinyl acetate (10 ml) was added and the reaction was allowed to proceed for a further 181/2 hours. The mixture was cooled to 2° and N aqueous sodium hydroxide (45 ml) was added. The layers were separated and the aqueous layer was extracted with ether (50 ml). The combined organic layers were washed with saturated brine (20 ml), dried over magnesium sulphate and concentrated on a rotary evaporator to give a yellow liquid (4.44 g) which was distilled under reduced pressure to give the title ethenyl ester (2.52 g); b.p. 43°-45°/ca 20 mm Hg.

Workup

  1. custom2 hours
  2. temperatureThe mixture was cooled to 2°
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ether (50 ml)
  5. washThe combined organic layers were washed with saturated brine (20 ml)
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-f2a051ad309d4d7aa0d61d37a8efcab0
Source dataset
uspto-grants-1986_07
Patent number
US04602012

Reaction notes

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