Acetic Acid → 2-Chloro-4-(trifluoromethoxy)phenol

HRID 2296331Notes

Reaction equation

HRID 2296331 reaction equation
C1(SC2C=CC=CC=2)C=CC=CC=1.[F:14][C:15]([F:25])([F:24])[O:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.C(O)(=O)C.S(Cl)([Cl:33])(=O)=O>C(Cl)Cl>[Cl:33][C:19]1[CH:18]=[C:17]([O:16][C:15]([F:24])([F:25])[F:14])[CH:22]=[CH:21][C:20]=1[OH:23]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8766Diphenyl sulfideHCID 24648Sulfuryl chlorideHCID 70015p-(Trifluoromethoxy)phenol

Product 1

HCID 130447832-Chloro-4-(trifluoromethoxy)phenolYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.05 part by weight of diphenyl sulfide is added to a solution of 8.9 parts by weight of 4-trifluoromethoxyphenol in 30 parts by weight of glacial acetic acid, and 6.8 parts by weight of sulfuryl chloride are then added dropwise, without cooling. The mixture is subsequently stirred at room temperature for 3 hours, the solvent is stripped off and the residue is taken up in 50 parts by weight of methylene chloride. This solution is twice washed with 50 parts by weight of saturated bicarbonate solution, and is dried and concentrated. Distillation of the residue under reduced pressure gives 9.8 parts by weight (92% of theory) of 2-chloro-4-trifluoromethoxyphenol of boiling point 70° C./13 mbar.

Workup

  1. additionare then added dropwise
  2. temperaturewithout cooling
  3. washThis solution is twice washed with 50 parts by weight of saturated bicarbonate solution
  4. customis dried
  5. concentrationconcentrated
  6. distillationDistillation of the residue under reduced pressure

Sources & evidence

ORD record
ord-0fc542c5f4064e8c9c068c1153210e55
Source dataset
uspto-grants-1984_01
Patent number
US04428944

Reaction notes

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