Benzene, 1,3-bis(chloromethyl)- → m-Xylylene glycol diacetate

HRID 2304000Notes

Reaction equation

HRID 2304000 reaction equation
[C:1]1([CH2:9]Cl)[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7]Cl)[CH:2]=1.[C:11]([O-:14])(=[O:13])[CH3:12].[K+]>CC(C)=O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:11]([O:14][CH2:9][C:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][O:14][C:11](=[O:13])[CH3:12])[CH:2]=1)(=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 12275Benzene, 1,3-bis(chloromethyl)-HCID 517044Potassium Acetate

Product 1

HCID 12571717m-Xylylene glycol diacetateYield 164.7%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 180AcetoneSolvent

Procedure

m-Xylylene dichloride (25.0 g, 143 mmol) and potassium acetate (34.0 g, 171 mmol) were suspended in acetone (125 ml). To the suspension was added benzyltriethylammonium chloride (4.8 g) and the mixture was refluxed for 2.5 hr. The reaction mixture was cooled and filtered. The solvent was evaporated and toluene (50 ml) was added. The toluene layer was washed with water (50 ml) and saturated brine (50 ml) and the solvent was evaporated to give m-xylylene glycol diacetate (31.3 g, 98.7%) as an oil.

Workup

  1. temperaturethe mixture was refluxed for 2.5 hr
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customThe solvent was evaporated
  5. additiontoluene (50 ml) was added
  6. washThe toluene layer was washed with water (50 ml) and saturated brine (50 ml)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8a59e5e51b9a4792a7ec5634bf8f951c
Source dataset
uspto-grants-2002_08
Patent number
US06433195B1

Reaction notes

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