Pinacolone → 1-Hydroxy-4,4-dimethylpent-1-en-3-one

HRID 1382484

Reaction equation

HRID 1382484 reaction equation
[CH3:1][C:2](=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4].[CH:8](OC)=[O:9]>C(OCC)C>[CH3:4][C:3]([CH3:6])([CH3:5])[C:2](=[O:7])[CH:1]=[CH:8][OH:9]

Participants

4

Reactant 2

HCID 6416PinacoloneHCID 7865Methyl formate

Product 1

HCID 405073641-Hydroxy-4,4-dimethylpent-1-en-3-oneYield 97.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
30 °C

Procedure

56.0 g (0.5 mole) of potassium tert.-butylate are added to a mixture of 50.0 g (0.5 mole) of pinacolone and 42.0 g (0.5 mole) of methyl formate at 15° to 20° C., with cooling. The reaction mixture is subsequently stirred at 30° C. for 12 hours. For working up, 400 ml of diethyl ether are added and the product precipitated is filtered off with suction and dried. 62.3 g (75% of theory) of 4,4-dimethyl-1-hydroxy-1-penten-3-one, as the potassium salt, are obtained in the form of a light yellow powder.

Workup

  1. temperaturewith cooling
  2. customthe product precipitated
  3. filtrationis filtered off with suction
  4. customdried

Sources & evidence

ORD record
ord-a52803208ca64874b92d541a6f8a99c0
Source dataset
uspto-grants-1989_02
Patent number
US04806644

Linked notes

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