Toluene → 1-(Allyl)pyrrolidin-2-one

HRID 1090343Notes

Reaction equation

HRID 1090343 reaction equation
C[O-].[Na+].[C:4]1(C)[CH:9]=CC=C[CH:5]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16].C(Cl)C=C>O>[CH2:9]([N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16])[CH:4]=[CH2:5]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7850Allyl chlorideHCID 120252-PyrrolidoneHCID 10942334Sodium Methoxide

Product 1

HCID 758971-(Allyl)pyrrolidin-2-oneYield 89.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 5 liter volume flask of glass equipped with a stirrer, a fractional distillation column, a thermometer and a dropping funnel, there were added 270.1 g (5.0 mol) of sodium methoxide and 2 liters of toluene. After 425.6 g (5.0 mol) of 2-pyrrolidone was dropwise added to the flask through the dropping funnel at room temperature, the resulting methanol was completely removed by the fractional distillation column. 6.9 g (25 mmol) of (Butyl-)4NCl was added as a phase transfer catalyst and 382.7 g (5.0 mol) of allyl chloride was dropwise added to the reaction mixture at a temperature ranging from 60° to 70° C. through the dropping funnel to react them. After the completion of the reaction, water was added to dissolve salts formed during the reaction and then the organic phase was removed. Then the organic phase was distilled to separate the fractions having a boiling point ranging from 75° to 76° C./4 mmHg. Thus, 562.5 g of 1-allyl-2-oxopyrrolidine was obtained in a yield of 89.9%.

Workup

  1. customTo a 5 liter volume flask of glass equipped with a stirrer
  2. distillationa fractional distillation column
  3. customthe resulting methanol was completely removed by the fractional distillation column
  4. additionwas dropwise added to the reaction mixture at a temperature
  5. customranging from 60° to 70° C. through the dropping funnel
  6. customto react them
  7. additionwas added
  8. dissolutionto dissolve salts
  9. customformed during the reaction
  10. customthe organic phase was removed
  11. distillationThen the organic phase was distilled
  12. customto separate the fractions
  13. customranging from 75° to 76° C.

Sources & evidence

ORD record
ord-b557131290ce4314915ddf22bbb0a36a
Source dataset
uspto-grants-1992_01
Patent number
US05081260

Reaction notes

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