Phenylacetaldehyde → HCID 9989863, compound

HRID 343914Notes

Reaction equation

HRID 343914 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-8d82f5523c6c4931a4d034aef45648c1
Source dataset
uspto-grants-1999_01
Patent number
US05863935

Reaction notes

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