Glutaric anhydride → HCID 15599090, compound

HRID 986800Notes

Reaction equation

HRID 986800 reaction equation
[NH:1]([C:8]1[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11]([OH:18])=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1(=[O:30])[O:29][C:27](=[O:28])[CH2:26][CH2:25][CH2:24]1.[OH-].[Na+]>O>[C:14]([C:12]1[CH:13]=[C:8]([CH:9]=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:11]=1[OH:18])[N:1]([C:23](=[O:30])[CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:15])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 7940Glutaric anhydrideHCID 14798Sodium HydroxideHCID 15599089HCID 15599089, compound

Product 1

HCID 15599090HCID 15599090, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

12.0 g (0.038 mole) of 4-anilino-2,6-di-t-butylphenol was added to a 55° C. melt of 12.0 g (0.105 mole) of glutaric anhydride. The reaction warmed to 90° C. during the addition. The reaction was allowed to cool to 50° C., and was then maintained at that temperature for 3 hours. Thereafter, the mixture was heated briefly to 80° C. and allowed to cool to room temperature. The reaction mass was ground to a powder and the powder was heated in water. This cloudy solution was allowed to cool, and was then basified with dilute sodium hydroxide, extracted twice with diethyl ether, and acidified with dilute hydrochloric acid. The resulting precipitate was collected, dried and recrystallized from a mixture of ethanol and water to give 8.9 g of white crystalline 5-(3,5-di-t-butyl-4-hydroxy-N-phenylanilino)-5-oxopentanoic acid, m.p. 168.5°-169° C. Analysis: Calculated for C25H33NO4 :% C, 73.0; % H, 8.1; % N, 3.4; Found: % C, 73.6; % H, 8.1; % N, 3.4.

Workup

  1. temperatureto cool to 50° C.
  2. temperaturewas then maintained at that temperature for 3 hours
  3. temperatureThereafter, the mixture was heated briefly to 80° C.
  4. temperatureto cool to room temperature
  5. temperatureto cool
  6. extractionextracted twice with diethyl ether
  7. customThe resulting precipitate was collected
  8. customdried
  9. customrecrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-386b9efba2ad483b8838da8ae1a7ba36
Source dataset
uspto-grants-1987_12
Patent number
US04716178

Reaction notes

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