Hydrochloric Acid → Phenyl 2-mercaptobenzoate

HRID 1086527Notes

Reaction equation

HRID 1086527 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[C:11]1(O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.P(Cl)(Cl)(Cl)=O.Cl>O>[C:1]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 996PhenolHCID 54432-Mercaptobenzoic AcidHCID 24813Phosphorus oxychloride

Product 1

HCID 84990Phenyl 2-mercaptobenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 250 ml three-necked flask a mixture of 69.4 g (0.45 mol) of thiosalicylic acid and 42.3 g (0.45 mol) of phenol is melted at 135° C. with stirring. Then, at 125°-130° C., 24.5 g (0.16 mol) of phosphorus oxychloride are added dropwise, HCl being liberated. When the addition is complete (about 15 min.) stirring is carried out for 30 minutes. The resulting dark-brown clear solution is stirred into 500 ml of water, a brown oil separating. This oil is taken up in ethyl acetate. The organic phase is extracted three times by shaking with soda solution, washed with water, dried and concentrated to a residue. The residue, which still contains phenol, is purified by distillation. The crude product is recrystallised from 250 ml of absolute methanol in the presence of activated carbon. The product is obtained in the form of colourless crystals having a melting point of 89° C. The yield is 36.0 g (=35% of the theoretical amount).

Workup

  1. additionWhen the addition
  2. custom(about 15 min.)
  3. stirringstirring
  4. customa brown oil separating
  5. extractionThe organic phase is extracted three times
  6. stirringby shaking with soda solution
  7. washwashed with water
  8. customdried
  9. concentrationconcentrated to a residue
  10. distillationThe residue, which still contains phenol, is purified by distillation
  11. customThe crude product is recrystallised from 250 ml of absolute methanol in the presence of activated carbon
  12. customThe product is obtained in the form of colourless crystals

Sources & evidence

ORD record
ord-dad0ed24195340c695c759d6837b88d6
Source dataset
uspto-grants-1991_07
Patent number
US05030671

Reaction notes

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