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

HRID 2166585Notes

Reaction equation

HRID 2166585 reaction equation
[OH-:1].[Na+].[Cl:3][C:4]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:5]=1[CH2:6]Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(O)(=O)C>[Cl:3][C:4]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:5]=1[CH2:6][OH:1]

Participants

5

Reactant 2

HCID 72122,4-Dichlorobenzyl chlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 156842,4-Dichlorobenzyl alcoholYield 95%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 176Acetic AcidSolvent

Procedure

Aqueous sodium hydroxide (36 ml. of 70% w/v solution) was added slowly with stirring to glacial acetic acid (39 g). The solution was then heated to reflux and a mixture of 2,4-dichlorobenzyl chloride (100 g) and tetrabutylammonium iodide (1 g) added. The mixture was heated under reflux with stirring for 7 hours. The mixture was then treated with aqueous sodium hydroxide and worked up as described in Example 1 to give 2,4-dichlorobenzyl alcohol, having a purity of 98.5% in a yield of 95.0%.

Workup

  1. temperatureThe solution was then heated
  2. temperatureto reflux
  3. additionadded
  4. temperatureThe mixture was heated
  5. temperatureunder reflux

Sources & evidence

ORD record
ord-98540ffa919d4f80afad731e148987a3
Source dataset
uspto-grants-1983_06
Patent number
US04387253

Reaction notes

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