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

HRID 555376Notes

Reaction equation

HRID 555376 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl.[NH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]1.C(N1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31])(OCC)=O>O>[OH:15][CH:12]1[CH2:13][CH2:14][CH:9]([N:8]2[C:25](=[O:26])[C:24]3[C:23](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:22]2=[O:31])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 178479278HCID 178479278, compound

Product 1

HCID 288726trans-2-(4-Hydroxycyclohexyl)-isoindole-1,3-dioneYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

K2CO3 (19.4 g, 140.6 mmol) was added to a solution of trans-4-aminocyclohexanol hydrochloride (9.0 g, 59.35 mmol) in water (150 mL) followed by N-carbethoxy phthalimide (18.8 g, 85.96 mmol). A white precipitate was formed immediately. Stirring continued at RT for 1 h. The precipitate was filtered off, washed with water and dried to afford 12 g (84%) of 2-(4-hydroxy-cyclohexyl)-isoindole-1,3-dione.

Workup

  1. customA white precipitate was formed immediately
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-ee7f18e56f3f4447af4c4028a29c4c1e
Source dataset
uspto-grants-2011_11
Patent number
US08053447B2

Reaction notes

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