Ethyl Acetate → HCID 54374521, compound

HRID 1029947Notes

Reaction equation

HRID 1029947 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)(O)[CH2:9][O:10]C)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 54243492HCID 54243492, compound

Product 1

HCID 54374521HCID 54374521, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 1,1-bis-(3-chlorophenyl)-2-methoxyethanol (47 g) (obtained by reaction of (3-chlorophenyl)magnesium bromide on methyl 2-methoxyacetate in tetrahydrofuran) in formic acid (44 cc) is refluxed for 5 hours, cooled and poured into a mixture of saturated sodium carbonate solution (500 cc) and ethyl acetate (300 cc). The organic phase is washed with water (3×250 cc) and with saturated sodium chloride solution (200 cc), then dried and concentrated to dryness under reduced pressure (2.7 kPa) to give bis-(3-chlorophenyl)acetaldehyde (36.9 g) in the form of a yellow oil.

Workup

  1. temperaturecooled
  2. washThe organic phase is washed with water (3×250 cc) and with saturated sodium chloride solution (200 cc)
  3. customdried
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-ae1f32dccf9b4d6ca70cb4e2b7f67fe2
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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