Acetic Acid → HCID 12769238, compound

HRID 1578224Notes

Reaction equation

HRID 1578224 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=O)[C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2.O[C:13]1[C:14]([Cl:21])=[C:15]([CH:17]=[CH:18][C:19]=1[Cl:20])[NH2:16].C(O)(=[O:24])C>O>[Cl:21][C:14]1[CH:13]=[C:19]([Cl:20])[C:18]([OH:24])=[CH:17][C:15]=1[N:16]1[C:1](=[O:11])[C:2]2[CH2:10][CH2:9][CH2:8][CH2:7][C:3]=2[C:4]1=[O:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 223925813-Amino-2,6-dichlorophenol

Product 1

HCID 12769238HCID 12769238, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 33.4 g. of 3,4,5,6-tetrahydrophthalic anhydride, 35.6 g. of 3-hydroxy-2,4-dichloroaniline and 130 ml. of glacial acetic acid was refluxed with stirring for 2 hours and the mixture was cooled to a room temperature and water was added to the mixture to precipitate a crystal. The crystal was separated by a filtration and recrystallized from benzene-n-hexane to obtain N-(2,4-dichloro-5-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide (m.p.: 155°-157° C.: white crystal) (yield: 75%).

Workup

  1. additionA mixture of 33.4 g
  2. customto precipitate a crystal
  3. customThe crystal was separated by a filtration
  4. customrecrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-642337c92c094b3c93d8292f49b9293e
Source dataset
uspto-grants-1981_09
Patent number
US04292070

Reaction notes

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