Salicylic Acid → 2,2,2-Trichloroethyl 2-hydroxybenzoate

HRID 1451133Notes

Reaction equation

HRID 1451133 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[Cl:11][C:12]([Cl:16])([Cl:15])[CH2:13]O.S(=O)(=O)(O)O>C(Cl)(Cl)Cl>[C:1]([O:10][CH2:13][C:12]([Cl:16])([Cl:15])[Cl:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

5

Reactant 3

HCID 338Salicylic AcidHCID 1118Sulfuric AcidHCID 8259Trichloroethanol

Product 1

HCID 131848122,2,2-Trichloroethyl 2-hydroxybenzoateYield 59.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

--A mixture of salicylic acid (90 g), 2,2,2-trichloroethanoI (270 g) and concentrated sulphuric acid (50 g) was stirred and heated at 100° C. for 4 hours. The mixture was diluted with chloroform (800 ml) and extracted with water (2×500 ml). After further extraction with saturated aqueous sodium bicarbonate solution (1000 ml), the organic layer was washed with water (2×500 ml) and dried (Mg SO4). The chloroform and excess trichloroethanol was removed in vacuo (65° C./20 mmHg) and the product was distilled (110°-112° C./0.5 mmHg) to give 2,2,2-trichloroethyl salicylate (104 g, 59% ) as a clear liquid which solidified on cooling.

Workup

  1. extractionextracted with water (2×500 ml)
  2. extractionAfter further extraction with saturated aqueous sodium bicarbonate solution (1000 ml)
  3. washthe organic layer was washed with water (2×500 ml)
  4. dry with materialdried (Mg SO4)
  5. customThe chloroform and excess trichloroethanol was removed in vacuo (65° C./20 mmHg)
  6. distillationthe product was distilled (110°-112° C./0.5 mmHg)

Sources & evidence

ORD record
ord-e95676bab0bf4157a5c8448941bb8911
Source dataset
uspto-grants-1997_02
Patent number
US05603959

Reaction notes

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