Sodium hydride → Phenyl p-(2-pyrrolidinoethoxy)benzoate

HRID 439327Notes

Reaction equation

HRID 439327 reaction equation
[OH:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:20][CH2:21][N:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>CN(C)C=O>[N:22]1([CH2:21][CH2:20][O:1][C:2]2[CH:16]=[CH:15][C:5]([C:6]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[O:7])=[CH:4][CH:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 816691-(2-Chloroethyl)pyrrolidineHCID 87250Phenylparaben

Product 1

HCID 22001247Phenyl p-(2-pyrrolidinoethoxy)benzoateYield 70.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

The title product was prepared as described iin U.S. Pat. No. 4,230,862. To 300 ml of N,N-dimethylformamide were added 107 grams of phenyl p-hydroxybenzoate and 26 grams of sodium hydride (50 percent in oil). The mixture was heated to 60° C. and maintained at this temperature for about two hours. To this mixture was added 1-chloro-2-pyrrolidin-1-ylethane (67 g), and the mixture was stirred overnight at 85° C. The bulk of the N,N-dimethylformamide then was evaporated from the mixture. Water was added to the residue, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate extract was concentrated, and the residue was dissolved in a 1:1 mixture of ether and ethyl acetate. The organic solution was then extracted with 2N hydrochloric acid, and the acid extract was added dropwise to 2N sodium hydroxide. The resulting mixture was extracted with ethyl acetate, and the ethyl acetate extract was washed and then dried over magnesium sulfate. The ethyl acetate was concentrated to obtain 110 grams of crude phenyl p-(2-pyrrolidin-1-ylethoxy)benzoate.

Workup

  1. temperaturemaintained at this temperature for about two hours
  2. customThe bulk of the N,N-dimethylformamide then was evaporated from the mixture
  3. additionWater was added to the residue
  4. extractionthe aqueous mixture was extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. concentrationwas concentrated
  7. dissolutionthe residue was dissolved in a 1:1 mixture of ether and ethyl acetate
  8. extractionThe organic solution was then extracted with 2N hydrochloric acid
  9. extractionthe acid extract
  10. additionwas added dropwise to 2N sodium hydroxide
  11. extractionThe resulting mixture was extracted with ethyl acetate
  12. extractionthe ethyl acetate extract
  13. washwas washed
  14. dry with materialdried over magnesium sulfate
  15. concentrationThe ethyl acetate was concentrated

Sources & evidence

ORD record
ord-85bc55a8e50040c59daae5a9eadf0730
Source dataset
uspto-grants-1996_05
Patent number
US05514675

Reaction notes

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