Dichloromethane → HCID 15870897, compound

HRID 582366Notes

Reaction equation

HRID 582366 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].[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:25][CH3:26])=[C:19]([C:23]=1[Cl:24])[C:20](Cl)=[O:21].[Cl-].[Al+3].[Cl-].[Cl-].ClCCl>C(OCC)(=O)C.O>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:25][CH3:26])=[C:19]([C:23]=1[Cl:24])[C:20]([C:4]1[C:5]([CH3:13])=[CH:6][C:7]([O:11][CH3:12])=[C:8]([O:9][CH3:10])[C:3]=1[O:2][CH3:1])=[O:21]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 809223,4,5-TrimethoxytolueneHCID 6451240Aluminum(III) ChlorideHCID 19598110HCID 19598110, compound

Product 1

HCID 15870897HCID 15870897, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3,4,5-trimethoxytoluene (0.83 g; 4.6 mmol), 4C (4.6 mmol), aluminium chloride (0.62 g, 4.6 mmol) and dichloromethane (20 ml) is stirred at room temperature for 3 hours. A mixture of water and ethyl acetate (1:1 v/v; 50 ml) is then added. The organic phase is concentrated and the residue is crystallized from diisopropylether and recrystallized from methanol. The solid material is collected by vacuum filtration, washed with water and dried yielding yellow crystals, 0.7 g, (35.4% y) mp 87-88° C.

Workup

  1. additionis then added
  2. concentrationThe organic phase is concentrated
  3. customthe residue is crystallized from diisopropylether
  4. customrecrystallized from methanol
  5. filtrationThe solid material is collected by vacuum filtration
  6. washwashed with water
  7. customdried
  8. customyielding yellow crystals, 0.7 g, (35.4% y) mp 87-88° C.

Sources & evidence

ORD record
ord-bcbcc3de2d494b7287de29de0f4c89ee
Source dataset
uspto-grants-1999_07
Patent number
US05922905

Reaction notes

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