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

HRID 2058553Notes

Reaction equation

HRID 2058553 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH3:9].Cl[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19].ClC(Cl)[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[Cl:29].[C:31](=[O:34])(O)[O-:32].[Na+]>O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[CH:11]=[O:32].[Cl:28][C:25]1[CH:24]=[C:23]([Cl:29])[CH:22]=[CH:27][C:26]=1[CH2:31][OH:34]

Participants

8

Reactant 4

HCID 72122,4-Dichlorobenzyl chlorideHCID 72542,4-DichlorotolueneHCID 86372,4-Dichloro-1-(dichloromethyl)benzeneHCID 516892Sodium Bicarbonate

Product 3

HCID 72542,4-DichlorotolueneYield 11.84%HCID 134042,4-DichlorobenzaldehydeYield 16.94%HCID 156842,4-Dichlorobenzyl alcoholYield 71.21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

To a 600 cc Hastoloy C autoclave was charged 48.52 g of a crude chlorination mixture containing 10.93% 2,4-dichlorotoluene, 70.39% α,2,4-trichlorotoluene, 18.52% α,α,2,4-tetrachlorotoluene, 0.10% α,α,2,4-pentachlorotoluene (the percentages represent gas chromatograph area percents), 39 g of sodium bicarbonate and 146 ml of water. The autoclave was flushed with nitrogen and pressure tested to 1500 psig. The autoclave was then vented to atmospheric pressure and heated. The temperature was increased to 160° C. and maintained for two hours. The pressure increased from atmosphere pressure to between 200 and 400 psig. After two hours, the autoclave was cooled to 80° C., vented and the product removed. After separation of the aqueous phase, the crude aldehyde mixture was flash distilled affording 11.84% 2,4-dichlorotoluene, 16.94% 2,4-dichlorobenzaldehyde and 71.21% 2,4-dichlorobenzyl alcohol.

Workup

  1. additionTo a 600 cc Hastoloy C autoclave was charged 48.52 g of a crude chlorination mixture
  2. customThe autoclave was flushed with nitrogen and pressure
  3. temperatureheated
  4. temperaturemaintained for two hours
  5. temperatureThe pressure increased from atmosphere pressure to between 200 and 400 psig
  6. temperaturethe autoclave was cooled to 80° C.
  7. customthe product removed
  8. customAfter separation of the aqueous phase
  9. distillationdistilled

Sources & evidence

ORD record
ord-08541278214043bc831c91b6bc57fb60
Source dataset
uspto-grants-1982_03
Patent number
US04317934

Reaction notes

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