Hydrochloric Acid → HCID 15599095, compound

HRID 986802Notes

Reaction equation

HRID 986802 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.[CH3:23][CH:24]1[CH2:30][C:29](=[O:31])[O:28][C:26](=[O:27])[CH2:25]1.Cl>[OH-].[Na+]>[C:14]([C:12]1[CH:13]=[C:8]([N:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:29]([CH2:30][CH:24]([CH3:23])[CH2:25][C:26]([OH:28])=[O:27])=[O:31])[CH:9]=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:11]=1[OH:18])([CH3:15])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 778283-Methylglutaric anhydrideHCID 15599089HCID 15599089, compound

Product 1

HCID 15599095HCID 15599095, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
140 °C

Procedure

Under a nitrogen atmosphere, a mixture of 2.97 g (0.01 mole) of 4-anilino-2,6-di-t-butylphenol and 6.40 g (0.05 mole) of 3-methylglutaric anhydride was heated at 140° C. for 2 hours. After cooling, the reaction mixture was suspended in 10% sodium hydroxide, and acidified with 10% hydrochloric acid. The resulting precipitate was collected, rinsed with water, air dried, and recrystallized twice from a mixture of ethyl acetate and hexane to give a beige solid. This material was purified by silica gel chromatography, eluting with ethyl acetate, followed by trituration with a mixture of ethyl acetate and hexane. The resulting solid was recrystallized from a mixture of ethyl acetate and hexane to give 2.3 g of white solid 4-[N-(3,5-di-t-butyl-4-hydroxyphenyl)-N-phenylcarbamoyl]-3-methylbutyric acid, m.p. 153°-155° C. Analysis: Calculated for C26H35NO4 :% C, 73.4; % H, 8.3; % N, 3.3 Found: % C, 73.4; % H, 8.6; % N, 3.1.

Workup

  1. temperatureAfter cooling
  2. customThe resulting precipitate was collected
  3. washrinsed with water, air
  4. customdried
  5. customrecrystallized twice from a mixture of ethyl acetate and hexane
  6. customto give a beige solid
  7. customThis material was purified by silica gel chromatography
  8. washeluting with ethyl acetate
  9. additionfollowed by trituration with a mixture of ethyl acetate and hexane
  10. customThe resulting solid was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-4e44536b065a46728ef4f04006a77ca5
Source dataset
uspto-grants-1987_12
Patent number
US04716178

Reaction notes

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