Water → 1,3-Dimethoxybenzene

HRID 541173Notes

Reaction equation

HRID 541173 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.O>C(OCC)(=O)C>[CH3:9][O:8][C:6]1[CH:7]=[CH:2][CH:3]=[C:4]([O:10][CH3:11])[CH:5]=1

Participants

4

Reactant 2

HCID 962WaterHCID 815021-Chloro-3,5-dimethoxybenzene

Product 1

HCID 90251,3-DimethoxybenzeneYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

86.3 mg (0.50 mmol) of 1-chloro-3,5-dimethoxybenzene (36), 45 μL (2.5 mmol) of distilled water and stainless steel balls (50 pieces) were placed in the vessel of the planetary ball mill, which was then closed, and agitated by operating the planetary ball mill for 30 minutes at 1,100 rpm. After the lapse of 30 minutes, 10 mL of ethyl acetate was added to the vessel of the ball mill to provide a solution containing the reaction mixture, which was then filtered with celite. The operation was repeated 5 times to provide a filtrate, which was then concentrated, thereby providing 36.6 mg (0.265 mmol) of 1,3-dimethoxybenzene (37). The yield was 53%. The reaction is expressed by the following scheme.

Workup

  1. customwas then closed
  2. customfor 30 minutes
  3. customto provide a solution
  4. additioncontaining the reaction mixture, which
  5. filtrationwas then filtered with celite
  6. customto provide a filtrate, which
  7. concentrationwas then concentrated

Sources & evidence

ORD record
ord-627474c5307143bb9220b310f94ee8b1
Source dataset
uspto-grants-2014_10
Patent number
US08871980B2

Reaction notes

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