Acetone → HCID 5375764, compound

HRID 1651349Notes

Reaction equation

HRID 1651349 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH3:15][C:16]([CH3:18])=[O:17].[OH-].[Na+]>O.Cl>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:4]=1/[CH:5]=[CH:15]/[C:16](=[O:17])[CH3:18]

Participants

6

Reactant 3

HCID 180AcetoneHCID 14798Sodium HydroxideHCID 750062,3,4-Trimethoxybenzaldehyde

Product 1

HCID 5375764HCID 5375764, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 19.6 g (0.1 mol) of 2,3,4-trimethoxybenzaldehyde in 21 ml (0.28 mol) of acetone and 10.5 ml of water was treated with 2.5 ml of 3N sodium hydroxide solution, whereby 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 ether/hexane 10:1). There was obtained (E)-4-(2,3,4-trimethoxyphenyl)but-3-en-2-one as a yellow oil. MS: 236 (M+), 205 (base peak) m/e.

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 ether/hexane 10:1)

Sources & evidence

ORD record
ord-56c82df3096f44ef9983cb7151b9b1d4
Source dataset
uspto-grants-1990_05
Patent number
US04927958

Reaction notes

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