Sodium Hydroxide → 116404-25-2

HRID 652235Notes

Reaction equation

HRID 652235 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH:16]([C:17]([O:19]C)=[O:18])[CH2:15][CH2:14][C:13]2=[O:21])=[CH:7][CH:6]=1>O>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:13](=[O:21])[CH2:14][CH2:15][CH:16]2[C:17]([OH:19])=[O:18])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12726696HCID 12726696, compound

Product 1

HCID 4191855116404-25-2Yield 48.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 16.80 g of sodium hydroxide pellets in 175 ml of water was treated with 75 g of (±)-1-[(4-methoxyphenyl)methyl]-5-methoxycarbonyl-2-pyrrolidinone and the mixture was heated for two hours with a steam bath. The solution was cooled to room temperature and extracted with diethyl ether (2×300 ml). The aqueous phase was acidified to about pH=1 with 50 ml of concentrated hydrochloric acid and extracted with dichloromethane (3×250 ml). The dried (Na2SO4) organic phase was vacuum filtered and concentrated to an oil which solidified on standing (80 g). The solid was recrystallized from toluene (300 ml) to give 34.18 g of crystals, m.p. 103°-104.5° C.

Workup

  1. temperaturethe mixture was heated for two hours with a steam bath
  2. extractionextracted with diethyl ether (2×300 ml)
  3. extractionextracted with dichloromethane (3×250 ml)
  4. dry with materialThe dried (Na2SO4) organic phase
  5. filtrationfiltered
  6. concentrationconcentrated to an oil which
  7. customThe solid was recrystallized from toluene (300 ml)

Sources & evidence

ORD record
ord-2977d96b51f1493b9d1a69f8209aca37
Source dataset
uspto-grants-1987_06
Patent number
US04670562

Reaction notes

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