Veratrole → 3,4-Dimethoxy-4'-methylbenzophenone

HRID 366615Notes

Reaction equation

HRID 366615 reaction equation
CO[C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1OC)[C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)=[O:7].[C:23]1(OC)C(=CC=CC=1)OC.[Cl-].[Al+3].[Cl-].[Cl-].CC1C=CC(C(Cl)=O)=CC=1>>[CH3:17][O:16][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[O:14][CH3:15])[C:6]([C:5]1[CH:4]=[CH:3][C:20]([CH3:23])=[CH:19][CH:18]=1)=[O:7]

Participants

5

Reactant 4

HCID 7043VeratroleHCID 134054-Methylbenzoyl ChlorideHCID 223042Bis(3,4-dimethoxyphenyl)methanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 15292913,4-Dimethoxy-4'-methylbenzophenone

Procedure

The title compound was prepared analogously to 3,4,3',4'-tetramethoxybenzophenone using veratrole (3.9 mL, 28 mmol), aluminum chloride (4.1 g, 31 mmol) and 4-methylbenzoyl chloride (4.6 mL, 29 mmol) with a reaction time of 6 hours at room temperature. The crude mixture was purified by flash column chromatography (silica gel, 2% ethyl acetate/methylene chloride) to afford 4.22 g (59%) of the product as a white solid: mp 121.5-122° C.; 1H NMR (CDCl3) δ 7.70-7.67 (d, J=8 Hz, 2 H), 7.48-7.26 (m, 4 H), 6.91-6.88 (d, J=8.3 Hz, 1 H), 6.96 (s, 3 H), 3.94 (s, 3 H), 2.44 (s, 3 H); 13C NMR (CDCl3) δ 195.1, 152.6, 148.8, 142.4, 135.3, 130.3, 129.8, 128.7, 125.0, 112.0, 109.6, 55.9, 55.8, 21.4; Anal. Calcd for C16H16O3. Theoretical: C, 74.98; H, 6.29. Found: C, 74.84; H, 6.43.

Workup

  1. customwith a reaction time of 6 hours
  2. customat room temperature
  3. customThe crude mixture was purified by flash column chromatography (silica gel, 2% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-aeff3d7604494073b0a321cb3d69eb4e
Source dataset
uspto-grants-2000_10
Patent number
US06130226

Reaction notes

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