Benzaldehyde → Benzaldehyde

HRID 1402776Notes

Reaction equation

HRID 1402776 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([O:15]CC)(=[O:14])[CH2:10][C:11]([CH3:13])=[O:12].N1CCCCC1>>[C:9]([O-:15])(=[O:14])[CH2:10][C:11]([CH3:13])=[O:12].[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 8082PiperidineHCID 8868Ethyl Acetoacetate

Product 2

HCID 240BenzaldehydeHCID 6971017Acetoacetate

Procedure

The mixture of benzaldehyde (21.22 g) and ethyl acetoacetate (52.06 g) was cooled in an ice bath. Piperidine (3.3 ml) was added with stirring. The resulting mixture was kept at rt for 3 days whereupon it solidifies. The solid was recrystallised from ethanol (100 ml) to give a light yellowish solid (the bis-adduct of acetoacetate to benzaldehyde). The powdered solid was added in portions to 50% NaOH (200 ml) with stirring. The resulting yellow slurry was diluted with ethanol (70 ml) and stirred at reflux for 2 h. After addition of ice water (100 ml) and cooling in an ice bath the mixture was acidified with conc. HCl to give a white precipitate. The solid was collected by suction filtration and washed with water. After drying in vacuo 3-phenylglutaric acid (16.4 g) was obtained as colourless crystals.

Workup

  1. temperaturewas cooled in an ice bath
  2. customThe solid was recrystallised from ethanol (100 ml)

Sources & evidence

ORD record
ord-0e178660abd34e9db8bd492b963b8192
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

Loading…