Glutaric anhydride → HCID 15598812, compound

HRID 1085386Notes

Reaction equation

HRID 1085386 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=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:23]1(=[O:30])[O:29][C:27](=[O:28])[CH2:26][CH2:25][CH2:24]1.C(COC)OC>O>[C:19]([C:10]1[CH:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][C:23](=[O:30])[CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH:13]=[C:12]([C:14]([CH3:15])([CH3:16])[CH3:17])[C:11]=1[OH:18])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 7940Glutaric anhydride2×HCID 80711,2-DimethoxyethaneHCID 20059576HCID 20059576, compound

Product 1

HCID 15598812HCID 15598812, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.9 g (6.4 mmole) of the known compound 2'-amino-3,5-di-tertiary-butyl-4-hydroxybiphenyl, 0.8 g (7.0 mmole) of glutaric anhydride and 50 ml of glyme was heated on a steam bath for three hours, then an additional 0.20 g of glutaric anhydride was added. The mixture was heated at reflux for six hours, then poured into water. The aqueous mixture was extracted with diethyl ether, and the ether extracts were then washed with 10% hydrochloric acid and water. The ether solution was extracted with dilute sodium carbonate solution, and the aqueous extracts were acidified to about pH 1 with 10% hydrochloric acid. An oil separated and crystallized after scratching to initiate crystal formation. Recrystallization of the residue from aqueous ethanol provided tan crystals of N-(3',5'-di-tertiary-butyl-4'-hydroxy-2-biphenylyl)glutaramic acid, m.p. 132°-134° C. Analysis: Calculated for C25H33NO4 : % C, 73.0; % H, 8.1; % N, 3.4; Found: % C, 73.0; % H, 8.0; % N, 3.3.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for six hours
  3. extractionThe aqueous mixture was extracted with diethyl ether
  4. washthe ether extracts were then washed with 10% hydrochloric acid and water
  5. extractionThe ether solution was extracted with dilute sodium carbonate solution
  6. customAn oil separated
  7. customcrystallized
  8. customRecrystallization of the residue from aqueous ethanol provided tan crystals of N-(3',5'-di-tertiary-butyl-4'-hydroxy-2-biphenylyl)glutaramic acid, m.p. 132°-134° C

Sources & evidence

ORD record
ord-eae696e7f01640f1b475829ef12e7c2b
Source dataset
uspto-grants-1991_04
Patent number
USRE033574

Reaction notes

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