Ethyl Acetate → HCID 54068354, compound

HRID 1029936Notes

Reaction equation

HRID 1029936 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F: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>[F:1][C:2]1[CH:3]=[C:4]([CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 537223311,1-Bis(3-fluorophenyl)-2-methoxyethanol

Product 1

HCID 54068354HCID 54068354, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 1,1-bis-(3-fluorophenyl)-2-methoxyethanol (156.7 g) (obtained by reaction of (3-fluorophenyl)magnesium bromide on methyl 2-methoxyacetate in THF) in formic acid (160 cc) is refluxed for 16 hours, cooled and poured into a mixture of saturated sodium carbonate solution (800 cc) and ethyl acetate (500 cc). The organic phase is washed with water (2×500 cc) and with saturated sodium chloride solution (500 cc) and then dried and concentrated to dryness under reduced pressure (2.7 kPa) to give bis-(3-fluorophenyl)acetaldehyde (144.5 g) in the form of a yellow oil.

Workup

  1. temperaturecooled
  2. washThe organic phase is washed with water (2×500 cc) and with saturated sodium chloride solution (500 cc)
  3. customdried
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-72b6cac6a2cc4f49b18bf295e82b24ae
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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