Water → 4-Anilinophenyl crotonate

HRID 26044

Reaction equation

HRID 26044 reaction equation
[C:1](Cl)(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[Na].[NH:8]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>C1C=CC=CC=1.[OH-].[Na+].C(O)C>[C:1]([O:21][C:18]1[CH:17]=[CH:16][C:15]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:20][CH:19]=1)(=[O:5])/[CH:2]=[CH:3]/[CH3:4]

Participants

8

Reactant 4

HCID 962WaterHCID 312084-Hydroxydiphenylamine2×HCID 643131trans-Crotonyl chlorideHCID 5360545Sodium

Product 1

HCID 211636064-Anilinophenyl crotonate

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-Anilinophenyl crotonate was prepared by adding a solution of 11.5 grams of crotonyl chloride in 50 milliliters of benzene to a solution of the sodium salt of 4-anilinophenol which was prepared by dissolving 18.5 grams of 4-anilinophenol in a solution of 4 grams of sodium hydroxide in 100 milliliters of ethanol. The addition was accomplished in 30 minutes and the reaction mixture was stirred for one hour. The mixture was then poured into 150 milliliters of water. The organic layer was separated, washed three times with 10 percent sodium hydroxide solution and once with water, dried over anhydrous sodium sulfate, then allowed to evaporate. The residue was recrystallized from hexane yielding 13.3 grams of product which melted at 73°-76° C.

Workup

  1. customwas prepared
  2. additionThe addition
  3. customThe organic layer was separated
  4. washwashed three times with 10 percent sodium hydroxide solution
  5. dry with materialonce with water, dried over anhydrous sodium sulfate
  6. customto evaporate
  7. customThe residue was recrystallized from hexane yielding 13.3 grams of product which melted at 73°-76° C.

Sources & evidence

ORD record
ord-3e50ab561b124247a9b9c228a91b812e
Source dataset
uspto-grants-1979_04
Patent number
US04147880

Linked notes

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