Ethyl Acetate → HCID 54162423, compound

HRID 1029953Notes

Reaction equation

HRID 1029953 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]([C:12]2[CH:13]=[C:14]([CH3:18])[CH:15]=[CH:16][CH:17]=2)(O)[CH2:8][O:9]C)[CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(O)=O>[C:14]1([CH3:18])[CH:15]=[CH:16][CH:17]=[C:12]([CH:7]([C:3]2[CH:2]=[C:1]([CH3:19])[CH:6]=[CH:5][CH:4]=2)[CH:8]=[O:9])[CH:13]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 54202865HCID 54202865, compound

Product 1

HCID 54162423HCID 54162423, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 1,1-bis-(3-tolyl)-2-methoxyethanol (24.66 g) (obtained by reaction of (3-tolyl)magnesium bromide on methyl 2-methoxyacetate in tetrahydrofuran) in formic acid (30 cc) is refluxed for 12 hours, cooled and poured into a mixture of saturated sodium carbonate solution (400 cc) and ethyl acetate (400 cc). The organic phase is washed with water (3×300 cc) and with saturated sodium chloride solution (300 cc), then dried and concentrated to dryness under reduced pressure (2.7 kPa) to give bis-(3-tolyl)acetaldehyde (20.45 g) in the form of a yellow oil.

Workup

  1. temperaturecooled
  2. washThe organic phase is washed with water (3×300 cc) and with saturated sodium chloride solution (300 cc)
  3. customdried
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-91ca2a935cc84ade861b51c7fe7099a2
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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