Succinic anhydride → HCID 15599091, compound

HRID 986799Notes

Reaction equation

HRID 986799 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[NH:8]([C:15]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:18]([OH:25])=[C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>COCCOC>[C:21]([C:19]1[CH:20]=[C:15]([CH:16]=[C:17]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:18]=1[OH:25])[N:8]([C:4](=[O:5])[CH2:3][CH2:2][C:1]([OH:6])=[O:7])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 7922Succinic anhydride2×HCID 15599089HCID 15599089, compound

Product 1

HCID 15599091HCID 15599091, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

1.5 g (0.015 mole) of succinic anhydride, 4.5 g (0.010 mole) of 4-anilino-2,6-di-t-butylphenol, and 10 ml of 1,2-dimethoxyethane were combined and heated at reflux for 48 hours. 1.5 g of succinic anhydride and 5 ml of 1,2-dimethoxyethane were added and the reaction was heated for an additional 24 hours. The reaction mixture was cooled in an ice bath. The resulting precipitate was collected, rinsed with a small amount of cold 1,2-dimethoxyethane, and recrystallized from a mixture of ethanol and water to give 3.7 g of off-white 4-(3,5-di-t-butyl-4-hydroxy-N-phenylanilino)-4-oxobutanoic acid, m.p. 205°-208° C. Analysis: Calculated for C24H31NO4 : % C, 72.5; % H, 7.9; % N, 3.5: Found: % C, 72.4; % H, 7.8; % N, 3.3.

Workup

  1. temperatureheated
  2. temperatureat reflux for 48 hours
  3. temperaturethe reaction was heated for an additional 24 hours
  4. temperatureThe reaction mixture was cooled in an ice bath
  5. customThe resulting precipitate was collected
  6. washrinsed with a small amount of cold 1,2-dimethoxyethane
  7. customrecrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-0362687f58bb4b218961bc8e094fbf4b
Source dataset
uspto-grants-1987_12
Patent number
US04716178

Reaction notes

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