Phenylacetaldehyde → HCID 9989863, compound

HRID 1608995Notes

Reaction equation

HRID 1608995 reaction equation
C[O-].[Na+].[N+:4]([CH3:7])([O-:6])=[O:5].[C:8]1([CH2:14][CH:15]=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[N+:4]([CH2:7][CH:15]([OH:16])[CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:6])=[O:5]

Participants

5

Reactant 3

HCID 998PhenylacetaldehydeHCID 6375NitromethaneHCID 10942334Sodium Methoxide

Product 1

HCID 9989863HCID 9989863, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium methoxide (1.1 g) was added to a stirred solution of nitromethane (Aldrich, 12.2 g) in methanol (100 ml) at 0° C. and the mixture stirred for 10 minutes. A solution of phenylacetaldehyde (Aldrich, 24.0 g) in methanol (50 ml) was added dropwise over 15 minutes and the mixture stirred for 45 minutes at 0° C., then brought to room temperature over 1 hour and stirred overnight. The mixture was evaporated in vacuo and the residue taken up in water and extracted with ether. The combined extracts were washed with water and brine and evaporated in vacuo to give the desired product as a yellow oil (29.0 g).

Workup

  1. stirringthe mixture stirred for 45 minutes at 0° C.
  2. waitbrought to room temperature over 1 hour
  3. stirringstirred overnight
  4. customThe mixture was evaporated in vacuo
  5. extractionextracted with ether
  6. washThe combined extracts were washed with water and brine
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6fadd21a52e8449d95c1c7420594a23e
Source dataset
uspto-grants-1995_03
Patent number
US05399574

Reaction notes

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