Veratrole → 2-(3,4-Dimethoxybenzoyl)furan

HRID 366627Notes

Reaction equation

HRID 366627 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:6]([C:8]1C=C[C:11]([O:14]C)=[C:10](OC)[CH:9]=1)=[O:7].C1(OC)C(=CC=CC=1)OC.[Cl-].[Al+3].[Cl-].[Cl-].O1C=CC=C1C(Cl)=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:6]([C:8]1[O:14][CH:11]=[CH:10][CH:9]=1)=[O:7]

Participants

5

Reactant 4

HCID 7043VeratroleHCID 682422-Furancarbonyl chlorideHCID 223042Bis(3,4-dimethoxyphenyl)methanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 8383262-(3,4-Dimethoxybenzoyl)furan

Procedure

2-(3,4-Dimethoxybenzoyl)furane was prepared analogously to 3,4,3',4'-tetramethoxybenzophenone using veratrole (1.3 mL, 10 mmol), aluminum chloride (1.5 g, 10 mmol) and 2-furoyl chloride (1.1 mL, 10 mmol) with a reaction time of 2 hours at reflux. The crude product was purified by flash column chromatography (silica gel, 4% ethyl acetate/methylene chloride) to afford 1.69 g (78%) of the product as a white solid: mp 112-114° C.; 1H NMR (CDCl3) δ 7.78-7.66 (m, 2 H), 7.59-7.52 (m, 1 H), 7.26-7.17 (m, 1 H), 6.96-6.90 (m, 1 H), 6.63-6.55 (m, 1 H), 3.97 (s, 3 H), 3.96 (s, 3 H); 13C NMR (CDCl3) δ 180.9, 153.0, 152.5, 148.9, 146.5, 129.8, 124.0, 119.6, 112.0, 111.7, 110.0, 56.0, 55.9; Anal. Calcd for C13H12O4. Theoretical: C, 67.23; H, 5.21. Found: C, 67.09; H, 5.21.

Workup

  1. customwith a reaction time of 2 hours
  2. temperatureat reflux
  3. customThe crude product was purified by flash column chromatography (silica gel, 4% ethyl acetate/methylene chloride)

Sources & evidence

ORD record
ord-0674f2ea61834746a6514a25383cc08f
Source dataset
uspto-grants-2000_10
Patent number
US06130226

Reaction notes

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