3,4,5,6-Tetrahydrophthalic anhydride → N-(4-chloro-5-hydroxymethylphenyl)-3,4,5,6-tetrahydrophthalimide

HRID 1681094Notes

Reaction equation

HRID 1681094 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.[Cl:12][C:13]1[C:19]([CH2:20][OH:21])=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1>C(O)(=O)C>[Cl:12][C:13]1[C:19]([CH2:20][OH:21])=[CH:18][C:16]([N:17]2[C:1](=[O:11])[C:2]3[CH2:10][CH2:9][CH2:8][CH2:7][C:3]=3[C:4]2=[O:6])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 13567962(5-Amino-2-chlorophenyl)methanol

Product 1

HCID 14277448N-(4-chloro-5-hydroxymethylphenyl)-3,4,5,6-tetrahydrophthalimideYield 38.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 50 ml of acetic acid, 2.47 g of 3,4,5,6-tetrahydrophthalic anhydride and2.56 g of 4-chloro-5-hydroxymethyl aniline were added and the mixture was heated to reflux under stirring for 16 hours. After cooling, the solvent was evaporated under reduced pressure and the residue was purified by column chromatography (silica gel, benzene/ethyl acetate=10/1 (v/v)) to obtain 1.82 g of the desired product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel, benzene/ethyl acetate=10/1 (v/v))

Sources & evidence

ORD record
ord-c17f1f7a1c5344879a1e59beccd67870
Source dataset
uspto-grants-1992_12
Patent number
US05169428

Reaction notes

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