Hydrochloric Acid → 2-(2,4-Dimethoxy-phenyl)-1-(2-hydroxy-4,6-dimethoxy-phenyl)-ethanone

HRID 1357058Notes

Reaction equation

HRID 1357058 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([O:22][CH3:23])=[CH:16][C:15]=1[O:24]C)=[O:13].[Al+3].[Cl-].[Cl-].[Cl-].Cl>ClC(Cl)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][C:12]([C:14]1[C:19]([O:20][CH3:21])=[CH:18][C:17]([O:22][CH3:23])=[CH:16][C:15]=1[OH:24])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 185054532-(2,4-Dimethoxyphenyl)-1-(2,4,6-trimethoxyphenyl)ethan-1-one

Product 1

HCID 125083652-(2,4-Dimethoxy-phenyl)-1-(2-hydroxy-4,6-dimethoxy-phenyl)-ethanoneYield 67.9%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

A solution of compound 6 (3.2 g, 9.3 mmol) and AICI3 (1.4 g, 10.2 mmol) in dichloroethane (30 mL) was heated to 60° C. for 15 minutes and additional AlCl3 (1.3 g) was added followed by an additional 15 minutes of heating at 60° C. The reaction was cooled and poured into 2 N HCl aq. The layers were separated and the organic phase was dried and concentrated to give a solid which was triturated with MeOH to give a white solid (2.1 g): Mp 116-119° C.; 1H NMR (CDCl3) δ 13.9 (s, 1H), 7.00 (d, 1H, J=8.0 Hz), 6.50-6.45 (m, 2H), 6.08 (d, 1H, J=2.4 Hz), 5.95 (d, 1H, J=2.4 Hz), 4.24 (s, 2H), 3.87 (s, 3H), 3.83 (s, 3H), 3.81 (s, 3H) 3.76 (s, 3H); MS FI 333 (M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. customwere separated
  3. customthe organic phase was dried
  4. concentrationconcentrated
  5. customto give a solid which
  6. customwas triturated with MeOH

Sources & evidence

ORD record
ord-e020b65114bc4700aed7c53da2df05db
Source dataset
uspto-grants-2003_07
Patent number
US06589980B2

Reaction notes

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