Acetone → 4-(2,3,4,5-Tetramethoxy-6-methylphenyl)but-3-en-2-one

HRID 1382688Notes

Reaction equation

HRID 1382688 reaction equation
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[C:8]([O:15][CH3:16])=[C:7]([CH3:17])[C:4]=1[CH:5]=O.[CH3:18][C:19]([CH3:21])=[O:20].C[O-].[Na+]>CO>[CH3:1][O:2][C:3]1[C:4]([CH:5]=[CH:18][C:19](=[O:20])[CH3:21])=[C:7]([CH3:17])[C:8]([O:15][CH3:16])=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 180AcetoneHCID 10942334Sodium MethoxideHCID 148523342,3,4,5-Tetramethoxy-6-methylbenzaldehyde

Product 1

HCID 542361174-(2,3,4,5-Tetramethoxy-6-methylphenyl)but-3-en-2-oneYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,3,4,5-tetramethoxy-6-methylbenzaldehyde (1.56 g, 6.5 mmol) and acetone (1.13 g, 19.5 mmol) in methanol (15 ml) was added 28% methanolic sodium methoxide (1.88 g). The mixture was refluxed for 1.5 hours. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was chromatographed on a silica gel column elution being carried out with isopropyl ether. The fractions containing the desired compound were concentrated to give 1,2,3,4-tetramethoxy-5-methyl-6-(3-oxo-1-butenyl)benzene (Compound 21, 1.09 g, 60% Oily substance) δ2.28 (3H), 2.36 (3H), 3.77 (3H), 3.79 (3H), 3.89 (3H), 3.95 (3H), 6.70 (1H), 7.57 (1H).

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. customAfter completion of the reaction
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was chromatographed on a silica gel column elution
  5. additionThe fractions containing the desired compound
  6. concentrationwere concentrated

Sources & evidence

ORD record
ord-8d452da21fe14e33bfeb661007617a78
Source dataset
uspto-grants-1989_02
Patent number
US04808339

Reaction notes

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