Acetone → 4-Nitro-3-(trifluoromethyl)benzenethiol

HRID 1415495Notes

Reaction equation

HRID 1415495 reaction equation
O.[S-2:2].[Na+].[Na+].Cl[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([C:15]([F:18])([F:17])[F:16])[CH:7]=1.CC(C)=O.Cl>O>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([SH:2])=[CH:7][C:8]=1[C:15]([F:18])([F:17])[F:16])([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 670525-Chloro-2-nitrobenzotrifluorideHCID 19906495Sodium sulfide monohydrate

Product 1

HCID 30160634-Nitro-3-(trifluoromethyl)benzenethiol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of sodium sulfide monohydrate 65.4 g. (0.276 moles) in 1 liter of water is treated with 50 g. (0.222 moles) of 4-chloro-2-trifluoromethylnitrobenzene in 500 ml. of acetone over 11/2 hour. The reaction mixture is stirred for 141/2 hours and the resultant solution treated with 25 ml. of concentrated hydrochloric acid. An oil separates from the reaction mixture which is dissolved in 200 ml. of ether, washed with water and extracted with 2.5 N sodium hydroxide solution. The aqueous solution is washed with ether and acidified with 25 ml. of hydrochloric acid. The resulting oil is extracted with ether and the ether solution washed with water affording 47 g. of 4-nitro-3-trifluoromethylbenzenethiol which is used in the next step.

Workup

  1. custom2 hour
  2. dissolutionis dissolved in 200 ml
  3. washof ether, washed with water
  4. extractionextracted with 2.5 N sodium hydroxide solution
  5. washThe aqueous solution is washed with ether
  6. extractionThe resulting oil is extracted with ether
  7. washthe ether solution washed with water affording 47 g

Sources & evidence

ORD record
ord-d7026da76ecd46a49451dff8089b17e4
Source dataset
uspto-grants-1977_01
Patent number
US04005199

Reaction notes

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