Hydrochloric Acid → HCID 15599097, compound

HRID 986803Notes

Reaction equation

HRID 986803 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:29])[O:28][C:26](=[O:27])[CH:25]=[CH:24]1.Cl.O>[OH-].[Na+].C(O)C>[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:23](=[O:29])/[CH:24]=[CH:25]\[C:26]([OH:28])=[O:27])[CH:9]=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:11]=1[OH:18])([CH3:15])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 7923Maleic AnhydrideHCID 15599089HCID 15599089, compound

Product 1

HCID 15599097HCID 15599097, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×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 4.90 g 0.05 mole) of maleic anhydride was heated at 140° C. for 2 hours. The cooled reaction mixture was suspended in 10% sodium hydroxide, and was then acidified with 10% hydrochloric acid. The resulting precipitate was collected, rinsed with water, air dried, and recrystallized from a mixture of ethyl acetate and hexane to give a yellow solid. This material was dissolved in hot ethanol. The ethanol solution was acidified with 6N hydrochloric acid, and then saturated with water. The resulting precipitate was collected, rinsed with water and air dried. This material was purified by silica gel chromatography, eluting with ethyl acetate, followed by recrystallization from a mixture of ethyl acetate and hexane to give 0.5 g of yellow crystalline N-(3,5-di-t-butyl-4-hydroxyphenyl)-N-phenylmaleamic acid, m.p. 154°-157° C. Analysis: Calculated for C25H29NO4 :% C, 72.9; % H, 7.9; % N, 3.5. Found: % C, 73.2; % H, 7.7; % N, 3.3.

Workup

  1. customThe cooled reaction mixture
  2. customThe resulting precipitate was collected
  3. washrinsed with water, air
  4. customdried
  5. customrecrystallized from a mixture of ethyl acetate and hexane
  6. customto give a yellow solid
  7. customThe resulting precipitate was collected
  8. washrinsed with water and air
  9. customdried
  10. customThis material was purified by silica gel chromatography
  11. washeluting with ethyl acetate
  12. customfollowed by recrystallization from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-2f99841eee904abe9686a3293420c602
Source dataset
uspto-grants-1987_12
Patent number
US04716178

Reaction notes

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