Potassium Hydroxide → Isoindolin-4-ylmethanol

HRID 1494848Notes

Reaction equation

HRID 1494848 reaction equation
C(OC([N:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[CH2:15][OH:16])[CH2:7]1)=O)C.[OH-].[K+]>C(O)(C)C.O>[OH:16][CH2:15][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[CH2:14][NH:6][CH2:7]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19828516HCID 19828516, compound

Product 1

HCID 19828510Isoindolin-4-ylmethanolYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

3.03 g of 2-ethoxycarbonyl-4-hydroxymethylisoindoline and 2.91 g of potassium hydroxide were dissolved in a mixture of 25 ml isopropyl alcohol and 2.5 ml of water. The mixture was heated under refluxing for 3 days. After the addition of water, the resulting reaction mixture was extracted with chloroform. The extract was washed with brine, concentrated, and recrystallized from carbontetrachloride to give 1.48 g of 4-hydroxymethylisoindoline.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder refluxing for 3 days
  3. customthe resulting reaction mixture
  4. extractionwas extracted with chloroform
  5. washThe extract was washed with brine
  6. concentrationconcentrated
  7. customrecrystallized from carbontetrachloride

Sources & evidence

ORD record
ord-bae8d62bff014f71a3d0c2b3ae13e759
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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