Water → HCID 20530813, compound

HRID 1833391Notes

Reaction equation

HRID 1833391 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]=1[OH:12])[CH2:5][CH:6]1[CH2:8][O:7]1.[C:17]1(=[O:23])[NH:21][C:20](=[O:22])[CH2:19][CH2:18]1.O>CN(C)C=O>[OH:7][CH:6]([CH2:5][C:4]1[CH:9]=[C:10]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:11]([OH:12])=[C:2]([CH3:1])[CH:3]=1)[CH2:8][N:21]1[C:17](=[O:23])[CH2:18][CH2:19][C:20]1=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 11439SuccinimideHCID 20530812HCID 20530812, compound

Product 1

HCID 20530813HCID 20530813, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6.6 g (0.03 mol) of 3-methyl-5-tert.-butyl-4-hydroxybenzyl-oxirane and 3 g (0.03 mol) of succinimide in 30 ml of dimethylformamide is stirred for 18 hours at a temperature of 150°-55° C whilst passing a slight stream of nitrogen through the mixture. After cooling to room temperature, the reaction mixture is poured into 150 ml of water and the oily reaction product which precipitates is dissolved in toluene. Successive extraction of the toluene phase with dilute hydrochloric acid, 5% strength aqueous sodium bicarbonate solution and water, drying over sodium sulphate and evaporation of the solvent gives the crude product. After recrystallisation from methylcellosolve, 6.5 g (68% of theory) of N-[2-hydroxy-3-(3-methyl-5-tert.-butyl-4-hydroxyphenyl)-propyl]-succinimide of melting point 217.5°-218° C are obtained in the form of colourless crystals.

Workup

  1. customthe oily reaction product which precipitates
  2. dissolutionis dissolved in toluene
  3. extractionSuccessive extraction of the toluene phase with dilute hydrochloric acid, 5% strength aqueous sodium bicarbonate solution and water
  4. dry with materialdrying over sodium sulphate and evaporation of the solvent

Sources & evidence

ORD record
ord-ab48f3446add46b19776a906203fd3b6
Source dataset
uspto-grants-1978_01
Patent number
US04066616

Reaction notes

Loading…