Acetone → HCID 56622311, compound

HRID 1165352Notes

Reaction equation

HRID 1165352 reaction equation
[C:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:14][C:15]([CH3:17])=[O:16].[OH-].[Na+]>C(O)(=O)C>[C:1]([O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[CH:14][C:15](=[O:16])[CH3:17])=[CH:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14798Sodium Hydroxide2×HCID 93774p-tert-Butoxybenzaldehyde

Product 1

HCID 56622311HCID 56622311, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

89 g (0.5 mole) of p-tert.-butoxy-benzaldehyde are added dropwise, in the course of 15 minutes, to a mixture of 290 g (5 moles) of acetone and 30 ml of 0.5% strength aqueous sodium hydroxide solution at 20°-25° C., whilst stirring. After all has been added, the pH must be not less than 10; if it is not, sodium hydroxide solution must then be added. The reaction is complete after about 5 hours, as is demonstrable by thin layer chromatography or gas chromatography. Acetic acid is then added to the solution until it is neutral, the excess acetone is distilled off under reduced pressure and the reaction product is taken up in ether. The ether solution is washed salt-free with water, the ether is distilled off and the reaction product is fractionated, giving 88 g of main fraction. This corresponds to a yield of 81% of theory.

Workup

  1. additionAfter all has been added
  2. distillationthe excess acetone is distilled off under reduced pressure
  3. washThe ether solution is washed salt-free with water
  4. distillationthe ether is distilled off
  5. customgiving 88 g of main fraction

Sources & evidence

ORD record
ord-887c8a92d6214a75bb5756cfa8dd63b3
Source dataset
uspto-grants-1990_03
Patent number
US04908481

Reaction notes

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