3-Methyl-2-buten-1-OL → 3-Methylbut-2-en-1-yl 3-oxobutanoate

HRID 370568Notes

Reaction equation

HRID 370568 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][OH:5].[CH2:7]=[C:8]1[O:12][C:10](=[O:11])[CH2:9]1>CCOCC.C([O-])(=O)C.[Na+]>[C:10]([O:5][CH2:4][CH:3]=[C:2]([CH3:6])[CH3:1])(=[O:11])[CH2:9][C:8]([CH3:7])=[O:12]

Participants

5

Reactant 2

HCID 111733-Methyl-2-buten-1-OLHCID 12661Diketene

Product 1

HCID 41734293-Methylbut-2-en-1-yl 3-oxobutanoateYield 76%

Reagents, catalysts & solvents 2

HCID 517045Sodium AcetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-methyl-2-buten-1-ol (21.2 g, 0.25 mole) and anhydrous sodium acetate (0.1 g) was cooled to 0°. Diketene (36 ml, 0.3 mole) was added dropwise over a period of 1.5 to 2 hours. The reaction mixture was then heated to 75°-80°, and this temperature was maintained for one hour. The mixture was diluted with ether. The ethereal solution was washed successively with aqueous 1N hydrochloric acid, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, and then dried over magnesium sulfate. The ether was evaporated, leaving a residue which was distilled under vacuum, affording 3-methyl-2-butenyl acetoacetate (32.1 g, 76% yield); bp 114°-117°/18-19 mm.

Workup

  1. temperaturewas cooled to 0°
  2. temperatureThe reaction mixture was then heated to 75°-80°
  3. temperaturethis temperature was maintained for one hour
  4. washThe ethereal solution was washed successively with aqueous 1N hydrochloric acid, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customThe ether was evaporated
  7. customleaving a residue which
  8. distillationwas distilled under vacuum

Sources & evidence

ORD record
ord-37d5d49cff774245a8baa9ec84d61fbb
Source dataset
uspto-grants-1985_07
Patent number
US04526987

Reaction notes

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