Benzaldehyde → HCID 178418547, compound

HRID 4718

Reaction equation

HRID 4718 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 was 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. customseparated 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-61f54da028b24a72bc1f764a9ad4f9e4
Source dataset
uspto-grants-1988_02
Patent number
US04727151

Linked notes

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