Acetic Acid → HCID 67041709, compound

HRID 2116694Notes

Reaction equation

HRID 2116694 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].C(O)(=O)C.S(Cl)([Cl:22])(=O)=O>O>[Cl:22][C:10]1[CH:9]=[C:5]([CH:4]=[C:3]([C:11]([F:12])([F:13])[F:14])[C:2]=1[OH:1])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24648Sulfuryl chloride2×HCID 27751124-Hydroxy-3-(trifluoromethyl)benzoic acid

Product 1

HCID 67041709HCID 67041709, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 11.7 g (57 mmol) 4-hydroxy-3-trifluoromethyl-benzoic acid and 40 ml acetic acid was combined dropwise with 5.15 ml (63 mmol) sulphurylchloride, with stirring at a bath temperature of 40° C., and stirred for 2 hours at 40° C. Then another 2.5 ml (31 mmol) sulphurylchloride were added and the mixture was stirred for 4 hours at 60° C. The reaction mixture was poured onto 300 ml of water and extracted with 200 ml EtOAc. The organic phase washed twice with 500 ml of water, dried and evaporated down under reduced pressure. The residue was stirred with 80 ml petroleum ether, the precipitate was suction filtered, washed with 20 ml petroleum ether and dried.

Workup

  1. stirringstirred for 2 hours at 40° C
  2. stirringthe mixture was stirred for 4 hours at 60° C
  3. extractionextracted with 200 ml EtOAc
  4. washThe organic phase washed twice with 500 ml of water
  5. customdried
  6. customevaporated down under reduced pressure
  7. stirringThe residue was stirred with 80 ml petroleum ether
  8. filtrationfiltered
  9. washwashed with 20 ml petroleum ether
  10. customdried

Sources & evidence

ORD record
ord-d7a96077cc28493197bccc2c0e403279
Source dataset
uspto-grants-2008_10
Patent number
US07439237B2

Reaction notes

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