Veratrole → 2',5'-Dichloro-3,4-dimethoxybenzophenone

HRID 583476Notes

Reaction equation

HRID 583476 reaction equation
COC1C=C(C=CC=1OC)C(C1C=CC(OC)=C(OC)C=1)=O.[C:23]1([O:31][CH3:32])[C:24](=[CH:27][CH:28]=[CH:29][CH:30]=1)[O:25][CH3:26].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:37][C:38]1[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:39]=1[C:40](Cl)=[O:41]>>[Cl:37][C:38]1[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:39]=1[C:40](=[O:41])[C:29]1[CH:28]=[CH:27][C:24]([O:25][CH3:26])=[C:23]([O:31][CH3:32])[CH:30]=1

Participants

5

Reactant 4

HCID 7043VeratroleHCID 179452,5-Dichlorobenzoyl chlorideHCID 223042Bis(3,4-dimethoxyphenyl)methanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 215846132',5'-Dichloro-3,4-dimethoxybenzophenone

Procedure

2',5'-Dichloro-3,4-dimethoxybenzophenone was prepared analogously to 3,4,3',4'-tetramethoxybenzophenone using veratrole (2.15 mL, 15 mmol), aluminum chloride (2.2 g, 16.5 mmol) and 2,5-dichlorobenzoyl chloride (1.9 mL, 15 mmol) with a reaction time of 3 hours at reflux. The crude product was purified by flash column chromatography (silica gel, 2.5% ethyl acetate/methylene chloride) to afford 3.88 g (83%) of the product as a white solid: mp 129-130° C.; 1H NMR (CDCl3) δ 7.65-7.56 (m, 1H), 7.41-7.12 (m, 4H), 6.89-6.81 (m, 1H), 3.96 (s, 3H), 3.94 (s, 3H); 13C NMR (CDCl3) δ 191.1, 154.4, 149.6, 137.9, 132.0, 130.5, 128.7, 128.0, 125.7, 110.2, 56.1, 56.0; Anal. Calcd for C15H12C2O3. Theoretical: C, 57.90; H, 3.89. Found: C, 57.58; H, 3.87.

Workup

  1. customwith a reaction time of 3 hours
  2. temperatureat reflux
  3. customThe crude product was purified by flash column chromatography (silica gel, 2.5% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-14b32fcb71c84b9b8e581feabd0aab46
Source dataset
uspto-grants-1999_07
Patent number
US05929117

Reaction notes

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