Sulfuric Acid → 1-Chloro-3-(4-chlorophenoxy)propan-2-one

HRID 328632Notes

Reaction equation

HRID 328632 reaction equation
[Cl:1][CH2:2][CH:3]([OH:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.O.O.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].S(=O)(=O)(O)O>O>[Cl:1][CH2:2][C:3](=[O:13])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 108005Sodium dichromate dihydrateHCID 2432501-chloro-3-(4-chlorophenoxy)propan-2-ol

Product 1

HCID 197652961-Chloro-3-(4-chlorophenoxy)propan-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred suspension of 44.2 parts of 1-chloro-3-(p-chlorophenoxy)-2-propanol in 75 parts of water are added 32.3 parts of sodium dichromate dihydrate. Then there is added dropwise, during a 5-hour period, a solution of 45 parts of sulfuric acid in 25 parts of water at a temperature <30° C. Upon completion, stirring is continued for 48 hours. The reaction mixture is poured onto water and the product is extracted twice with diisopropyl ether. The combined extracts are washed three times with water, dried, filtered and evaporated. The residue solidifies on scratching in ether. The solid product is crystallized from diisopropyl ether, yielding 25.2 parts of 1-chloro-3-(p-chlorophenoxy)-2-propanone.

Workup

  1. additionThen there is added dropwise, during a 5-hour period
  2. customat a temperature <30° C
  3. additionThe reaction mixture is poured onto water
  4. extractionthe product is extracted twice with diisopropyl ether
  5. washThe combined extracts are washed three times with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe solid product is crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-647ff33a394b49f1b6f451e4282a2040
Source dataset
uspto-grants-1977_04
Patent number
US04017631

Reaction notes

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