Acetone → 4-(4-Methylphenyl)-3-buten-2-one

HRID 38665

Reaction equation

HRID 38665 reaction equation
O.[OH-].[Na+].[CH3:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1.Cl.[CH3:14][C:15]([CH3:17])=[O:16]>>[CH3:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[CH:14][C:15](=[O:16])[CH3:17])=[CH:7][CH:6]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 962WaterHCID 77254-MethylbenzaldehydeHCID 14798Sodium Hydroxide

Product 1

HCID 1073884-(4-Methylphenyl)-3-buten-2-oneYield 45.6%

Procedure

Water (20 ml) and 10% NaOH aqueous solution (4 ml) were added under stirring to the solution of 4-methylbenzaldehyde (10.2 g, 10 mmol) in acetone (10 ml). The reaction mixture was stirred for 14 hr at room temperature, then the pH value was adjusted to pH=7.0 with 10% hydrochloric acid, extracted with methylene chloride. The combined methylene chloride extract was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated to give 0.73 g of a yellow viscous oil, yield: 45.6%.

Workup

  1. extractionextracted with methylene chloride
  2. extractionThe combined methylene chloride extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-454981ae6c944075b3f892a7abf49cbe
Source dataset
uspto-grants-2013_09
Patent number
US08524744B2

Linked notes

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