Hydrochloric Acid → 6,6'-Dimethyl-2,2',3',4'-tetramethoxy-benzophenone

HRID 611705Notes

Reaction equation

HRID 611705 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH3:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:14][O:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:17]=1[C:18](Cl)=[O:19].[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(OCC)(=O)C.ClCCl>[CH3:25][C:21]1[C:17]([C:18]([C:4]2[C:5]([CH3:13])=[CH:6][C:7]([O:11][CH3:12])=[C:8]([O:9][CH3:10])[C:3]=2[O:2][CH3:1])=[O:19])=[C:16]([O:15][CH3:14])[CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 809223,4,5-TrimethoxytolueneHCID 6451240Aluminum(III) ChlorideHCID 128926752-Methoxy-6-methylbenzoyl chloride

Product 1

HCID 154310606,6'-Dimethyl-2,2',3',4'-tetramethoxy-benzophenone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3,4,5-trimethoxytoluene (1.86 g; 10.2 mmol), 1B (10.2 mmol), aluminium chloride (1.33 g, 10 mmol) and dichloromethane (20 ml) is stirred at 0° C. The reaction sets up at 0° C. with formation of hydrogen chloride. Subsequently, the reaction mixture is stirred for another 4 hours at room temperature. A mixture of dilute hydrochloric acid and ethyl acetate (1:1 v/v; 100 ml) is then slowly added at 0° C. The organic phase is concentrated and the residue is recrystallized from methanol. The solid material is collected by vacuum filtration, three times washed with methanol/water (3:1 v/v; 100 ml each) and dried yielding white crystals, 1.0 g (30.3%), mp 84° C.

Workup

  1. stirringSubsequently, the reaction mixture is stirred for another 4 hours at room temperature
  2. additionis then slowly added at 0° C
  3. concentrationThe organic phase is concentrated
  4. customthe residue is recrystallized from methanol
  5. filtrationThe solid material is collected by vacuum filtration, three times
  6. washwashed with methanol/water (3:1 v/v; 100 ml each)
  7. customdried
  8. customyielding white crystals, 1.0 g (30.3%), mp 84° C.

Sources & evidence

ORD record
ord-4ace90345f304c50b8fe97ed6f3d1249
Source dataset
uspto-grants-1999_12
Patent number
US06001883

Reaction notes

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