Sulfuric Acid → Crotonic acid 2,2,2-trichloroethyl ester

HRID 249533

Reaction equation

HRID 249533 reaction equation
C(Cl)(Cl)(Cl)Cl.[C:6]([OH:11])(=[O:10])/[CH:7]=[CH:8]/[CH3:9].[Cl:12][C:13]([Cl:17])([Cl:16])[CH2:14]O.S(=O)(=O)(O)O>O>[Cl:12][C:13]([Cl:17])([Cl:16])[CH2:14][O:10][C:6](=[O:11])/[CH:7]=[CH:8]/[CH3:9]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5943Carbon TetrachlorideHCID 8259TrichloroethanolHCID 637090Crotonic Acid

Product 1

HCID 15703159Crotonic acid 2,2,2-trichloroethyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In 200 ml. carbon tetrachloride are dissolved 0.5 mole (43.07 g.) crotonic acid and the equimolar amount of 2,2,2-trichloroethanol, 1 ml. concentrated sulphuric acid is added thereto and the reaction mixture is heated under reflux on a water separator until the theoretical amount of water (9 ml.) has separated off. Subsequently, the organic phase is shaken out twice with, in each case, 100 ml. aqueous 2N sodium hydrogen carbonate solution and twice with, in each case, 50 ml. of water, the organic phase is then dried with anhydrous magnesium sulphate and the solvent is distilled off in a vacuum. There is finally obtained the desired product (i) in the form of a bright yellow oil in a yield of 95% of theory. C6H7O2Cl3. (217.4791).

Workup

  1. temperaturethe reaction mixture is heated
  2. customhas separated off
  3. dry with materialof water, the organic phase is then dried with anhydrous magnesium sulphate
  4. distillationthe solvent is distilled off in a vacuum

Sources & evidence

ORD record
ord-f50bdbb835e34209bf80adf5c63d8046
Source dataset
uspto-grants-1993_05
Patent number
US05214195

Linked notes

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