Acetic Acid → 4,4,4-Trichloro-2-(3,5-dichlorophenyl)butane-1,2-diol

HRID 1075739Notes

Reaction equation

HRID 1075739 reaction equation
[Cl:1][C:2]([Cl:15])([Cl:14])[CH2:3][C:4]([C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[CH:7]=1)=[CH2:5].C(O)(=[O:18])C.C(OO)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH2:36]>S(=O)(=O)(O)O.C(Cl)Cl.CO>[Cl:15][C:2]([Cl:14])([Cl:1])[CH2:3][C:4]([C:6]1[CH:7]=[C:8]([Cl:13])[CH:9]=[C:10]([Cl:12])[CH:11]=1)([OH:18])[CH2:5][OH:36]

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 962Water2×HCID 6101p-Toluenesulfonic acidHCID 6585Peracetic AcidHCID 92617Benzene, 1,3-dichloro-5-(3,3,3-trichloro-1-methylenepropyl)-

Product 1

HCID 156146284,4,4-Trichloro-2-(3,5-dichlorophenyl)butane-1,2-diol

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
60 °C

Procedure

α-(2,2,2-trichloroethyl)-3,5-dichlorostyrene (10.0 grams, 0.033 mole) was mixed with 75 ml. of glacial acetic acid and 10 drops of concentrated sulfuric acid and 16.5 ml. of 40% peracetic acid were added thereto. The resulting reaction mixture was heated at about 60° C., with stirring, for a period of about 72 hours. The reaction mixture was subsequently diluted with 200 ml. of water and 200 ml. of methylene chloride. The organic layer of the resulting mixture was separated and washed successively with 2-100 ml. portions of water, 2-100 ml. portions of a 10% sodium carbonate solution, 100 ml. portion of a 5% sodium bisulfite solution and another 100 ml. portion of water. The organic layer of the resulting mixture was separated therefrom, dried over sodium sulfate and the solvent removed in vacuo. The residual oil thus obtained was dissolved in about 75 ml. of methanol and 0.3 gram of p-toluenesulfonic acid were added thereto. The resulting mixture was heated under reflux conditions for a period of about 11 hours and then cooled and diluted with 200 ml. of water and 200 ml. of methylene chloride. The organic layer of the resulting mixture was separated, dried over sodium sulfate. The solvent was removed in vacuo to obtain the desired 4,4,4-trichloro-2-(3,5-dichlorophenyl)-2-hydroxybutanol product as a clear oily liquid.

Workup

  1. customThe resulting reaction mixture
  2. additionThe reaction mixture was subsequently diluted with 200 ml
  3. customThe organic layer of the resulting mixture was separated
  4. washwashed successively with 2-100 ml
  5. customThe organic layer of the resulting mixture was separated
  6. dry with materialdried over sodium sulfate
  7. customthe solvent removed in vacuo
  8. customThe residual oil thus obtained
  9. dissolutionwas dissolved in about 75 ml
  10. temperatureThe resulting mixture was heated under reflux conditions for a period of about 11 hours
  11. temperaturecooled
  12. additiondiluted with 200 ml
  13. customThe organic layer of the resulting mixture was separated
  14. dry with materialdried over sodium sulfate
  15. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-e20c82ef412d483fb8f9c28257f6bf7d
Source dataset
uspto-grants-1976_05
Patent number
US03954440

Reaction notes

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