Veratrole → 2-(3,4-Dimethoxybenzoyl)-6-methylpyridine

HRID 256209Notes

Reaction equation

HRID 256209 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8](Cl)=[O:9])[CH:5]=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24]>ClCC(Cl)(Cl)Cl>[CH3:15][O:16][C:17]1[CH:22]=[C:21]([CH:20]=[CH:19][C:18]=1[O:23][CH3:24])[C:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1)=[O:9]

Participants

5

Reactant 3

HCID 7043VeratroleHCID 6451240Aluminum(III) ChlorideHCID 143305406-Methylpyridine-2-carbonyl chloride

Product 1

HCID 126232692-(3,4-Dimethoxybenzoyl)-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 124181,1,1,2-TetrachloroethaneSolvent

Procedure

To an ice-cooled, stirred suspension of 6-methylpicolinic acid chloride and 2 equivalents of aluminum chloride in tetrachloroethane is added slowly an equivalent amount of 1,2-dimethoxybenzene. The reaction mixture is allowed to come to room temperature overnight, then decomposed over cracked ice. Extractive workup followed by chromotography of the organic residue gives the desired ketone.

Sources & evidence

ORD record
ord-5a53c470ba2b4df6a5b37956791260ab
Source dataset
uspto-grants-1987_10
Patent number
US04701461

Reaction notes

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