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

HRID 366620Notes

Reaction equation

HRID 366620 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]1[CH:13]=[CH:12][C:11](OC)=[C:10](OC)[CH:9]=1)=[O:7].[C:23]1(OC)[C:24](=CC=[CH:29][CH:30]=1)OC.[Cl-].[Al+3].[Cl-].[Cl-].C1C2C(=CC=CC=2)C=CC=1C(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[CH:13]=[CH:12][C:11]2[C:10](=[CH:24][CH:23]=[CH:30][CH:29]=2)[CH:9]=1)=[O:7]

Participants

5

Reactant 4

HCID 7043VeratroleHCID 752462-Naphthoyl chlorideHCID 223042Bis(3,4-dimethoxyphenyl)methanoneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 110771812-(3,4-Dimethoxybenzoyl)naphthalene

Procedure

2-(3,4-Dimethoxybenzoyl)naphthalene was prepared analogously to 3,4,3',4'-tetramethoxybenzophenone using veratrole (2.6 mL, 20 mmol), aluminum chloride (2.9 g, 22 mmol) and 2-naphthoyl chloride (3.9 g, 20 mmol) with a reaction time of 4 hours at reflux. The crude product was purified by flash column chromatography (silica gel, 2.5% ethyl acetate/methylene chloride) to afford 4.52 g (77%) of the product as a white solid: mp 120-121.5° C.; 1H NMR (CDCl3) δ 8.24 (s, 1 H), 8.03-7.84 (m, 4 H), 7.68-7.40 (m, 4 H), 7.00-6.87 (m, 1 H), 3.97 (s, 3 H), 3.95 (s, 3 H); 13C NMR (CDCl3) δ 195.5, 153.0, 149.0, 135.5, 134.9, 132.2, 131.0, 130.4, 129.2, 128.1, 128.0, 127.8, 126.7, 125.9, 125.4, 112.2, 109.8, 56.1, 56.0; Anal. Calcd for C19H16O3. Theoretical: C, 78.06; H, 5.52. Found: C, 77.73; H, 5.69.

Workup

  1. customwith a reaction time of 4 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-9d0002149b7641d1b398ab2b8ff1d8d6
Source dataset
uspto-grants-2000_10
Patent number
US06130226

Reaction notes

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