Hydrochloric Acid → 4-Anilinophenyl hydrogen maleate

HRID 1606415Notes

Reaction equation

HRID 1606415 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.[K].[NH:9]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.Cl>CC(C)([O-])C.[K+].O.C(O)(C)(C)C>[C:4]([O:22][C:19]1[CH:18]=[CH:17][C:16]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:21][CH:20]=1)(=[O:5])/[CH:3]=[CH:2]\[C:1]([OH:6])=[O:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7923Maleic AnhydrideHCID 312084-Hydroxydiphenylamine2×HCID 5462222Potassium2×

Product 1

HCID 706089004-Anilinophenyl hydrogen maleate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 23665647Potassium tert-butoxideSolvent

Procedure

4-Anilinophenyl hydrogen maleate was prepared by adding 10 grams of maleic anhydride to a solution of the potassium salt of 4-anilinophenol which was prepared by dissolving 18.5 grams of 4-anilinophenol in a solution of potassium tert.butoxide prepared by reacting 3.9 grams of potassium with 75 milliliters of tert.butyl alcohol. The reaction mixture was stirred for 2 hours at 65°-70° C. and was then poured into a solution of 12 milliliters of concentrated hydrochloric acid in 138 milliliters of water. The organic layer was separated by extraction with benzene. The extract was washed twice with water and then allowed to evaporate. The residue was recrystallized twice from benzene yielding 1.3 grams of product which melted at 139°-142° C.

Workup

  1. customwas prepared
  2. customprepared
  3. customThe organic layer was separated by extraction with benzene
  4. washThe extract was washed twice with water
  5. customto evaporate
  6. customThe residue was recrystallized twice from benzene yielding 1.3 grams of product which melted at 139°-142° C.

Sources & evidence

ORD record
ord-3f33899e93004d5d81a08a275de29a58
Source dataset
uspto-grants-1976_04
Patent number
US03953411

Reaction notes

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