Toluene → trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dione

HRID 569100Notes

Reaction equation

HRID 569100 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1.[C:10]1(=O)[O:15][C:13](=[O:14])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.C(N(C(C)C)C(C)C)C.C1(C)C=CC=CC=1>O>[C:10]1(=[O:15])[N:2]([CH:3]2[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]2)[C:13](=[O:14])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12

Participants

6

Reactant 4

HCID 1140TolueneHCID 6811Phthalic AnhydrideHCID 81531DiisopropylethylamineHCID 522619(1s,4s)-4-Aminocyclohexan-1-ol hydrochloride

Product 1

HCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

75.5 g (0.5 Mol) of 4-aminocyclohexanolhydrochloride and 74.0 g (0.5 Mol) of phthalic acid anhydride are mixed with 65 g (0.5 Mol) of ethyl-diisopropyl-amine and 1000 ml of toluene and boiled for 36 hours with a water separator. Then water is added, the toluene phase is separated off and the aqueous phase is extracted several times with chloroform. The organic phases are combined, dried and concentrated. The concentration residue is recrystallised from isopropanol.

Workup

  1. customthe toluene phase is separated off
  2. extractionthe aqueous phase is extracted several times with chloroform
  3. customdried
  4. concentrationconcentrated
  5. customThe concentration residue is recrystallised from isopropanol

Sources & evidence

ORD record
ord-dc1b9f2c2d714ce2b6be12f9d0a79744
Source dataset
uspto-grants-1988_03
Patent number
US04731374

Reaction notes

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