Veratrole → HCID 21584605, compound

HRID 366635Notes

Reaction equation

HRID 366635 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-].[CH3:37][O:38][C:39]1[CH:47]=[CH:46][CH:45]=[C:44]([O:48][CH3:49])[C:40]=1[C:41](Cl)=[O:42]>>[CH3:49][O:48][C:44]1[CH:45]=[CH:46][CH:47]=[C:39]([O:38][CH3:37])[C:40]=1[C:41](=[O:42])[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 748102,6-Dimethoxybenzoyl chlorideHCID 223042Bis(3,4-dimethoxyphenyl)methanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21584605HCID 21584605, compound

Procedure

2',6',3,4-Tetramethoxybenzophenone was prepared analogously to 3,4,3',4'-tetramethoxybenzophenone except using veratrole (1.3 mL, 10 mmol), aluminum chloride (1.47 g, 11 mmol) and 2,6-dimethoxybenzoyl chloride (2.0 mL, 10 mmol) with a reaction time of 24 hours at room temperature. The crude mixture was purified by flash column chromatography (silica gel, 4% ethyl acetate/methylene chloride) to afford 2.11 g (70%) of the product as a white solid: mp 128-129° C.; 1H NMR (CDCl3) δ 7.66-7.60 (m, 1 H), 7.40-7.20 (m, 2 H), 6.88-6.79 (m, 1 H), 6.67-6.65 (m, 2 H), 3.93 (s, 3 H), 3.91 (s, 3 H), 3.71 (s, 6 H); 13C NMR (CDCl3) δ 193.8, 157.4, 153.4, 148.9, 130.9, 130.5, 125.3, 118.0, 110.2, 109.9, 104.0, 55.9, 55.8; Anal. Calcd for C17H18O5. Theoretical: C, 67.54; H, 6.00. Found: C, 66.51; H, 5.91.

Workup

  1. customwith a reaction time of 24 hours
  2. customat room temperature
  3. customThe crude mixture was purified by flash column chromatography (silica gel, 4% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-b96a8418d44c43a7837b96203ecd66d6
Source dataset
uspto-grants-2000_10
Patent number
US06130226

Reaction notes

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