Acetaldehyde → HCID 19899897, compound

HRID 1029902Notes

Reaction equation

HRID 1029902 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])([O-])=O.[CH:14](=O)[CH3:15].[CH2:17](O)[CH3:18]>[Pd]>[CH2:17]([N:1]([CH2:14][CH3:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][C:11]([OH:13])=[O:12])[CH3:18]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 702EthanolHCID 77337(2-Nitrophenyl)acetic acid

Product 1

HCID 19899897HCID 19899897, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2-Diethylaminonphenylacetic acid is prepared by hydrogenation of a suspension of 2-nitrophenylacetic acid (9 g) in ethanol (40 cc) under a pressure of 7 bar for 4 hours at 25° C. in the presence of acetaldehyde (7 cc) and 10% palladium-on-carbon black (1 g). The reaction mixture is filtered, the filtrate is concentrated to dryness under reduced pressssure (2.7 kPa) and the residue is chromatographed on a silica column (0.2-0.063 mm, diameter 5 cm, height 50 cm), eluting under a nitrogen pressure of 0.7 bar with a mixture of cyclohexane and ethyl acetate (70/30 by volume) and collecting 125 cc fractions. Fractions 38 to 48 are concentrated to dryness under reduced pressure (2.7 kPa) to give 2-diethylaminophenylacetic acid (1.1 g) in the form of a yellow oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated to dryness under reduced pressssure (2.7 kPa)
  3. customthe residue is chromatographed on a silica column (0.2-0.063 mm, diameter 5 cm, height 50 cm)
  4. washeluting under a nitrogen pressure of 0.7 bar
  5. additionwith a mixture of cyclohexane and ethyl acetate (70/30 by volume)
  6. customcollecting 125 cc fractions
  7. concentrationFractions 38 to 48 are concentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-f4d179008f1648d28d5c5e17ae236d3f
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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