Acetone → HCID 19010860, compound

HRID 1741835Notes

Reaction equation

HRID 1741835 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19])[CH2:6]P(=O)(OCC)OCC.[CH3:22][C:23]([CH3:25])=O.[H-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:23]([CH3:25])[CH3:22])[CH:15]=[CH:16][C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 180AcetoneHCID 311Citric AcidHCID 24758Sodium hydrideHCID 53661922HCID 53661922, compound

Product 1

HCID 19010860HCID 19010860, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of diethyl (3-methoxy-4-methoxycarbonylbenzyl)phosphonate (1.28 g) and acetone (1.5 ml) in N,N-dimethylformamide (5 ml) was added 60% sodium hydride-oil dispersion (162 mg). The reaction mixture was stirred at room temperature for 14 hours and then poured into ice-cooled 10% citric acid. The mixture was extracted with ether and the organic layer was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of n-hexane and ethyl acetate (85:15) to give methyl 2-methoxy-4-(2-methyl-1propenyl)benzoate (184 mg) as an oil.

Workup

  1. additionpoured into ice-
  2. extractionThe mixture was extracted with ether
  3. washthe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel column
  7. washeluting with a mixture of n-hexane and ethyl acetate (85:15)

Sources & evidence

ORD record
ord-c835a3e0712c41c09694f49c9137ca39
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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