Veratrole → (3,4-Dimethoxyphenyl)(4-methoxyphenyl)methanone

HRID 971017Notes

Reaction equation

HRID 971017 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14].[CH3:15][O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1>C(Cl)Cl>[CH3:5][O:6][C:7]1[CH:12]=[C:11]([C:21]([C:20]2[CH:24]=[CH:25][C:17]([O:16][CH3:15])=[CH:18][CH:19]=2)=[O:22])[CH:10]=[CH:9][C:8]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 7043VeratroleHCID 7477p-Anisoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2754574(3,4-Dimethoxyphenyl)(4-methoxyphenyl)methanoneYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Aluminum chloride (2.15 g, 16.12 mmol) was added to a stirred mixture of 1,2-dimethoxybenzene (2.03 g, 14.65 mmol) in anhydrous methylene chloride (20 ml) in an ice bath. Then a solution of 4-methoxybenzoyl chloride (2.50 g, 14.65 mmol) in anhydrous methylene chloride (50 ml) was added. The mixture was allowed to warm up to rt, then refluxed overnight. After cooling down to rt, the mixture was poured to ice water (50 ml), stirred for 20 min., and extracted with methylene chloride (3×50 ml). The combined organic extracts were washed with sat. NaHCO3 (3×50 ml), H2O (2×50 ml), brine (50 ml), dried over MgSO4, filtered and concentrated in vacuo to an oil, which was purified via flash column chromatography (10% EtOAc in hexane) to give (3,4-dimethoxy-phenyl)-(4-methoxy-phenyl)methanone as an off-white solid (3.66 g, 92%); 1HNMR (CDCl3) δ 7.80 (d, J=8 Hz, 2H, Ar), 7.44 (d, J=1 Hz, 12H, Ar), 7.37 (dd, J=1 Hz and 8 Hz, 1H, Ar), 6.97 (d, J=8 Hz, 2H, Ar), 6.90 (d, J=8 Hz, 1H), 3.96 (s, 3H, OCH3), 3.94 (s, 3H, OCH3), 3.89 (s, 3H, OCH3). The product was carried over to the next step.

Workup

  1. temperaturerefluxed overnight
  2. temperatureAfter cooling down to rt
  3. extractionextracted with methylene chloride (3×50 ml)
  4. washThe combined organic extracts were washed with sat. NaHCO3 (3×50 ml), H2O (2×50 ml), brine (50 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to an oil, which
  8. customwas purified via flash column chromatography (10% EtOAc in hexane)

Sources & evidence

ORD record
ord-ca91c02104034455bba6c01f0d170b2f
Source dataset
uspto-grants-2007_12
Patent number
US07312241B2

Reaction notes

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