2,4-Dichlorobenzyl chloride → 2,4-Dichlorobenzyl alcohol

HRID 2166584Notes

Reaction equation

HRID 2166584 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Cl.C([O-])(=[O:13])C.[Na+].[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:13]

Participants

6

Reactant 3

HCID 72122,4-Dichlorobenzyl chlorideHCID 14798Sodium HydroxideHCID 517045Sodium Acetate

Product 1

HCID 156842,4-Dichlorobenzyl alcoholYield 94.6%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

2,4-Dichlorobenzyl chloride (100 g) was added to a solution of sodium acetate (208.8 g) and tetrabutylammonium hydrogen sulphate (2 g) in water. The mixture was heated under reflux with stirring for 25 hours. Aqueous sodium hydroxide (50 ml. of 70% w/v solution) was added and the refluxing continued for 30 minutes. The mixture was cooled and the solid collected by filtration, washed with water and dried in vacuo to give 2,4-dichlorobenzyl alcohol, having a purity of 99.3%, in a yield of 94.6%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. waitthe refluxing continued for 30 minutes
  4. temperatureThe mixture was cooled
  5. filtrationthe solid collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-252eda5914444d23a9c7ae6e2d47244b
Source dataset
uspto-grants-1983_06
Patent number
US04387253

Reaction notes

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