Hydrochloric Acid → 3-Hydroxy-4-chloro-1-(beta,beta,beta-trichloroethoxycarbonyl)-pyrrolidine

HRID 971678Notes

Reaction equation

HRID 971678 reaction equation
[O:1]1[CH:6]2[CH:2]1[CH2:3][N:4]([C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])[CH2:5]2.[ClH:15]>O1CCOCC1.O>[OH:1][CH:2]1[CH:6]([Cl:15])[CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:13])[Cl:12])=[O:8])[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131922053,4-Epoxy-1-(beta,beta,beta-trichloroethoxycarbonyl)-pyrrolidine

Product 1

HCID 131922063-Hydroxy-4-chloro-1-(beta,beta,beta-trichloroethoxycarbonyl)-pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4.0 g of 3,4-epoxy-1-(β,β,β-trichloroethoxycarbonyl)-pyrrolidine are dissolved in 15 ml of dioxane, and the solution is treated with 50 ml of 6 N hydrochloric acid. The slightly exothermic reaction is kept at room temperature by means of a water bath, and the reaction mixture is stirred for 15 hours, then diluted with water and extracted 3 times with 100 ml of methylene chloride. The organic phase is washed with 0.1 N sodium hydroxide solution and then with aqueous sodium chloride solution, dried over sodium sulphate and then evaporated to dryness, first under a water pump vacuum and then under a high vacuum, 3-hydroxy-4-chloro-1-(β,β,β-trichloroethoxycarbonyl)-pyrrolidine being obtained as a slightly yellow oil.

Workup

  1. customThe slightly exothermic reaction
  2. customis kept at room temperature by means of a water bath
  3. extractionextracted 3 times with 100 ml of methylene chloride
  4. washThe organic phase is washed with 0.1 N sodium hydroxide solution
  5. dry with materialwith aqueous sodium chloride solution, dried over sodium sulphate
  6. customevaporated to dryness, first under a water pump vacuum

Sources & evidence

ORD record
ord-0504b306d8a948488d92c26b090c2276
Source dataset
uspto-grants-1979_07
Patent number
US04160837

Reaction notes

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