Pyrrolidone carboxylic acid → HCID 11287601, compound

HRID 1607122Notes

Reaction equation

HRID 1607122 reaction equation
[NH:1]1[CH:5]([C:6]([OH:8])=[O:7])[CH2:4][CH2:3][C:2]1=[O:9].[CH2:10](O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[CH2:10]([O:7][C:6]([CH:5]1[NH:1][C:2](=[O:9])[CH2:3][CH2:4]1)=[O:8])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 499Pyrrolidone carboxylic acidHCID 1118Sulfuric AcidHCID 8129HeptanolHCID 516892Sodium Bicarbonate

Product 1

HCID 11287601HCID 11287601, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 200-ml eggplant-shaped flask equipped with a condenser and a mechanical stirrer was charged with 6.5 g (0.05 mole) of 2-pyrrolidone-5-carboxylic acid, 23.2 g (0.20 mole) of n-heptyl alcohol, a catalytic amount of concentrated sulfuric acid and 40 ml of benzene and the mixture was refluxed for 3.5 hours. The reaction mixture was cooled to room temperature and poured into saturated aqueous NaHCO3, followed by extraction with benzene. Washing, drying, solvent removal and distillation under reduced pressure as performed in the conventional manner gave 7.4 g of yellow 2-pyrrolidone-5-carboxylic acid n-heptyl ester. Boiling point: 186°-188° C./3 mm Hg.

Workup

  1. customA 200-ml eggplant-shaped flask equipped with a condenser and a mechanical stirrer
  2. extractionfollowed by extraction with benzene
  3. washWashing
  4. customdrying
  5. customsolvent removal and distillation under reduced pressure

Sources & evidence

ORD record
ord-62051e1abc95426dabf51fc06e529210
Source dataset
uspto-grants-1989_09
Patent number
US04863952

Reaction notes

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