Anisole → Ethyl 2-(4-methoxyphenyl)-2-oxoacetate

HRID 2299704Notes

Reaction equation

HRID 2299704 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].Cl[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:13]1([O:19][CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[CH3:20][O:19][C:13]1[CH:18]=[CH:17][C:16]([C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7519AnisoleHCID 20884Ethoxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2758864Ethyl 2-(4-methoxyphenyl)-2-oxoacetateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of aluminum chloride (59.0 g) and dichloromethane (500 ml), ethyl chloroglyoxylate (45.4 ml) was added dropwise at 0° C. After stirring for 15 minutes, anisole (40.1 ml) was added dropwise at 0° C., and the mixture was stirred for 1.5 hours at room temperature. The reaction mixture was poured onto ice (500 g), and the mixture was stirred for 1 hour at room temperature. The dichloromethane layer separated was washed with saturated aqueous sodium chloride, dried (MgSO4), and then concentrated. The residue was subjected to column chromatography on silica gel, and ethyl 4-methoxyphenylglyoxylate (43.6 g, yield 60%) was obtained as an oil from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Workup

  1. additionwas added dropwise at 0° C
  2. stirringthe mixture was stirred for 1.5 hours at room temperature
  3. additionThe reaction mixture was poured onto ice (500 g)
  4. stirringthe mixture was stirred for 1 hour at room temperature
  5. customThe dichloromethane layer separated
  6. washwas washed with saturated aqueous sodium chloride
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-566d04ac7c304a77a5ac97e9c95af846
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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