Benzaldehyde → HCID 178418547, compound

HRID 971472Notes

Reaction equation

HRID 971472 reaction equation
[C:1]([Cl:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.[CH:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[K+].[Br-]>CCOCC>[Cl-:9].[C:16]([O:8][CH:1]([N+:13]1[CH:14]=[CH:15][N:11]([CH3:10])[CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 13901-MethylimidazoleHCID 7412Benzoyl chlorideHCID 253877Potassium Bromide

Product 1

HCID 178418547HCID 178418547, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ether solution of benzoyl chloride 2.81 g (0.02 mol) there was added dropwise 1.67 g (0.02 mol) 1-methylimidazole with stirring. The resulting mixture was evaporated in vacuo and the residue was allowed to react with 2.12 g (0.02 mol) benzaldehyde at 70° overnite. After cooling, the reaction mixture was triturated with ether and the solid separated by filtration. Recrystallization from dichloromethane:dioxane gave 4.2 g (0.012 mol), 65%, 9, mp 199°-201°; ir (KBr) 1740 cm-1 ; pmr (CDCl3) δ 4.17 (s, 3H), 8.18-7.25 (m, 12H), 8.50 (s, 1H) and 11.1 (bs, 1H) ppm.

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. temperatureAfter cooling
  3. customthe reaction mixture was triturated with ether
  4. customthe solid separated by filtration
  5. customRecrystallization from dichloromethane
  6. customdioxane gave 4.2 g (0.012 mol), 65%, 9, mp 199°-201°

Sources & evidence

ORD record
ord-69b6b95935b74bb6a1a30c15b9a7205b
Source dataset
uspto-grants-1979_07
Patent number
US04160099

Reaction notes

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