Diphenyl Ether → Ethyl 4-phenoxybenzoylformate

HRID 584350Notes

Reaction equation

HRID 584350 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][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[O:19]([C:20]1[CH:21]=[CH:22][C:23]([C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:24][CH:25]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 20884Ethoxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2758881Ethyl 4-phenoxybenzoylformateYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of aluminum chloride (29.3 g) and dichloromethane (250 ml), ethyl chloroglyoxylate (22.3 ml) was added dropwise at 0° C. After stirring for 30 minutes, diphenyl ether (63.5 ml) was added dropwise over 30 minutes at 0° C. followed by stirring for 2 hours, the reaction mixture was poured onto ice (250 g) and stirred for 1 hour at room temperature. The dichloromethane layer was separated, washed with saturated aqueous sodium chloride, dried (MgSO4), and then concentrated. The residue was subjected to column chromatography on silica gel, and ethyl 4-phenoxyphenylglyoxylate (38.0 g, yield 70%) was obtained as an oil from a fraction eluted with ethyl acetate-hexane (1:10, v/v).

Workup

  1. additionwas added dropwise at 0° C
  2. stirringby stirring for 2 hours
  3. additionthe reaction mixture was poured onto ice (250 g)
  4. stirringstirred for 1 hour at room temperature
  5. customThe dichloromethane layer was separated
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4d8b22b00b234c1a8ba0342310244c28
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

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