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

HRID 1730207Notes

Reaction equation

HRID 1730207 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-chloro3-(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-49100463ac9b4f1d9047a1607f194d52
Source dataset
uspto-grants-1976_11
Patent number
US03991202

Reaction notes

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