Acetone → HCID 11095766, compound

HRID 1651359Notes

Reaction equation

HRID 1651359 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1[CH:5]=O.[CH3:13][C:14]([CH3:16])=[O:15].[OH-].[Na+]>O.Cl>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:4]=1/[CH:5]=[CH:13]/[C:14](=[O:15])[CH3:16]

Participants

6

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 667262,5-Dimethoxybenzaldehyde

Product 1

HCID 11095766HCID 11095766, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 16.6 g (0.1 mol) of 2,5-dimethoxybenzaldehyde in 21 ml (0.28 mol) of acetone and 10 ml of water was treated with 2.5 ml of 3N sodium hydroxide solution. The temperature of the reaction mixture should not exceed 30°. The mixture was stirred at room temperature for 20 hours, diluted with water and 3N hydrochloric acid was added to produce a strongly acidic reaction. The aqueous phase was extracted twice with methylene chloride. The combined organic phases were washed with water, dried over magnesium sulphate and concentrated. The residue was purified by flash chromatography on 1000 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1). There was obtained (E)-4-(2,5-dimethoxyphenyl)but-3-en-2-one as a yellow oil.

Workup

  1. customexceed 30°
  2. additionwas added
  3. customto produce
  4. customa strongly acidic reaction
  5. extractionThe aqueous phase was extracted twice with methylene chloride
  6. washThe combined organic phases were washed with water
  7. dry with materialdried over magnesium sulphate
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on 1000 g of silica gel (elution agent methylene chloride/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-192782d084ed4c91b5f12ae73c7f8b01
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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