Glutaric anhydride → HCID 15599090, compound

HRID 986798Notes

Reaction equation

HRID 986798 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[NH:9]([C:16]1[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:19]([OH:26])=[C:18]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>COCCOC>[C:22]([C:20]1[CH:21]=[C:16]([CH:17]=[C:18]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:19]=1[OH:26])[N:9]([C:5](=[O:6])[CH2:4][CH2:3][CH2:2][C:1]([OH:7])=[O:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 15599089HCID 15599089, compound

Product 1

HCID 15599090HCID 15599090, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1.1 g (0.010 mole) of glutaric anhydride, 3.0 g (0.010 mole) of the known compound 4-anilino-2,6-di-t-butylphenol, and 30 ml of 1,2-dimethoxyethane were combined and heated at reflux for 24 hours. The volume of the reaction was reduced by two-thirds under a stream of nitrogen, and the reaction was heated for another 24 hours. The remaining solvent was removed under vacuum on a rotary evaporator. The resulting solid was recrystallized twice from a mixture of benzene and hexane and then twice from a mixture of ethanol and water to give 0.6 g of off-white crystalline 5-(3,5-di-t-butyl-4-hydroxy-N-phenylanilino)- 5-oxopentanoic acid, m.p. 168°-170° C. Analysis: Calculated for C25H33NO4 : % C, 73.0; % H, 8.1; % N, 3.4: Found: % C, 73.2; % H, 8.0; % N, 3.0.

Workup

  1. temperatureheated
  2. temperatureat reflux for 24 hours
  3. temperaturethe reaction was heated for another 24 hours
  4. customThe remaining solvent was removed under vacuum on a rotary evaporator
  5. customThe resulting solid was recrystallized twice from a mixture of benzene and hexane
  6. additiontwice from a mixture of ethanol and water

Sources & evidence

ORD record
ord-b50a49cbdd7a4ce592e3f1241fc90837
Source dataset
uspto-grants-1987_12
Patent number
US04716178

Reaction notes

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