Methane, dichloromethoxy- → 2,3,4,5-Tetramethoxy-6-methylbenzaldehyde

HRID 2268489Notes

Reaction equation

HRID 2268489 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([O:10][CH3:11])=[C:5]([O:12][CH3:13])[C:4]=1[O:14][CH3:15].[CH3:16][O:17]C(Cl)Cl>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([O:14][CH3:15])=[C:5]([O:12][CH3:13])[C:6]([O:10][CH3:11])=[C:7]([CH3:9])[C:8]=1[CH:16]=[O:17]

Participants

5

Reactant 2

HCID 21004Methane, dichloromethoxy-HCID 98777642,3,4,5-Tetramethoxytoluene

Product 1

HCID 148523342,3,4,5-Tetramethoxy-6-methylbenzaldehyde

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,2,3,4-tetramethoxy-5-methylbenzene (20.0 g) in methylene chloride (100 ml) was dropwise added titanium tetrachloride (20.6 ml) with cooling with ice, followed by addition of 1,1-dichlorodimethylether (11.0 ml) with cooling with ice. The reaction mixture was allowed to warm to room temperature and further stirred for 8 hr. The reaction mixture was poured into ice-water, and extracted with diethyl ether. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=10:1) to give the entitled compound(21.5 g) as an oil.

Workup

  1. temperaturewith cooling with ice
  2. temperaturewith cooling with ice
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. customdried
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-5f21fe725ade48208bd1df3095463b35
Source dataset
uspto-grants-2001_12
Patent number
US06326369B1

Reaction notes

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