Phenol → trans-3-Hydroxy-4-phenoxy-1-(beta,beta,beta-trichloroethoxycarbonyl)-pyrrolidine

HRID 1389840Notes

Reaction equation

HRID 1389840 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.[C:15]1([OH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>C(#N)C.O>[OH:1][C@H:2]1[C@H:6]([O:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]([Cl:14])([Cl:12])[Cl:13])=[O:8])[CH2:3]1

Participants

6

Reactant 3

HCID 996PhenolHCID 14798Sodium HydroxideHCID 131922053,4-Epoxy-1-(beta,beta,beta-trichloroethoxycarbonyl)-pyrrolidine

Product 1

HCID 86736578trans-3-Hydroxy-4-phenoxy-1-(beta,beta,beta-trichloroethoxycarbonyl)-pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2.6 g (0.01 mol) of the 3,4-epoxy-1-(β,β,β-trichloroethoxycarbonyl)-pyrrolidine described in Example 1 are heated together with 1.88 g (0.02 mol) of phenol and 10 ml of 1 N sodium hydroxide solution in 30 ml of acetonitrile for 5 hours under reflux. After cooling, the reaction mixture is diluted with water and extracted 3 times with methylene chloride, and the organic phase is washed twice with 2 N sodium hydroxide solution and then once with water, dried over sodium sulphate and evaporated under a water pump vacuum. The resulting oil crystallises from methylene chloride/hexane and gives trans-3-hydroxy-4-phenoxy-1-(β,β,β-trichloroethoxycarbonyl)-pyrrolidine with a melting point of 100°-103°.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. extractionextracted 3 times with methylene chloride
  4. washthe organic phase is washed twice with 2 N sodium hydroxide solution
  5. dry with materialonce with water, dried over sodium sulphate
  6. customevaporated under a water pump vacuum
  7. customThe resulting oil crystallises from methylene chloride/hexane

Sources & evidence

ORD record
ord-b290d97c924a479eaaffa8f7e7ce2d4b
Source dataset
uspto-grants-1981_01
Patent number
US04246269

Reaction notes

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