Hydrochloric Acid → 2,4-Dichloro-alpha-(chloromethyl)benzenepropanol

HRID 1390602Notes

Reaction equation

HRID 1390602 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[Cl:10].[Mg].[Cl:12][CH2:13][CH:14]1[CH2:16][O:15]1.Cl>O(CC)CC>[Cl:10][C:4]1[CH:5]=[C:6]([Cl:9])[CH:7]=[CH:8][C:3]=1[CH2:2][CH2:16][CH:14]([CH2:13][Cl:12])[OH:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 72122,4-Dichlorobenzyl chlorideHCID 7835EpichlorohydrinHCID 5462224Magnesium

Product 1

HCID 204768722,4-Dichloro-alpha-(chloromethyl)benzenepropanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred and refluxing Grignard-complex, previously prepared starting from 98 parts of 1-(chloromethyl)-2,4-dichlorobenzene and 14 parts of magnesium in 70 parts of 1,1-oxybisethane, is added dropwise a solution of 46.5 parts of 2-(chloromethyl)oxirane in 350 parts of 1,1'-oxybisethane. Upon completion, stirring at reflux temperature is continued overnight. The reaction mixture is cooled in an ice-bath and decomposed by dropwise addition of 120 parts of a concentrated hydrochloric acid solution. The whole is poured onto water and the layers are separated. The organic phase is washed three times with water. The aqueous phase is extracted with 1,1'-oxybisethane. The combined organic phases are dried, filtered and evaporated. The residue is distilled, yielding 2,4-dichloro-α-(chloromethyl)benzenepropanol; bp. 130° C. at 0.04 mm. pressure.

Workup

  1. temperaturerefluxing Grignard-complex
  2. custompreviously prepared
  3. stirringUpon completion, stirring
  4. temperatureat reflux temperature
  5. temperatureThe reaction mixture is cooled in an ice-bath
  6. additionThe whole is poured onto water
  7. customthe layers are separated
  8. washThe organic phase is washed three times with water
  9. extractionThe aqueous phase is extracted with 1,1'-oxybisethane
  10. customThe combined organic phases are dried
  11. filtrationfiltered
  12. customevaporated
  13. distillationThe residue is distilled

Sources & evidence

ORD record
ord-a7550d53dba14c3a9ad28f6a35d02bba
Source dataset
uspto-grants-1979_02
Patent number
US04139540

Reaction notes

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