Carbon Dioxide → HCID 58930456, compound

HRID 915651Notes

Reaction equation

HRID 915651 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].S(=O)(=O)(O)O.[CH3:21][C:22](=[CH2:24])[CH3:23].C(=O)=O>ClCCl.CC(C)=O>[C:22]([O:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])([CH3:24])([CH3:23])[CH3:21]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 701602-(3-Hydroxypropyl)isoindoline-1,3-dione

Product 1

HCID 58930456HCID 58930456, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

Dissolve 2-(3-hydroxypropyl)isoindole-1,3-dione (2 g, 9.74 mmol, 1 eq) in 40 mL of dichloromethane under N2. Add sulfuric acid (780 μL) and cool reaction mixture to −5° C. Condense isobutylene gas to a liquid using a −78° C. cold finger charged with dry ice and acetone. Add approximately 20 mL of the condensed liquid to the reaction mixture and slowly warm the solution to room temperature overnight while stirring. Add saturated, aqueous sodium hydrogencarbonate to the reaction mixture and extract product into the organics. Wash separated organic layer with water and dry over magnesium sulfate to give 1.969 g (77% yield) of 2-(3-tert-butoxypropyl)isoindole-1,3-dione as a colorless oil.

Workup

  1. customreaction mixture to −5° C
  2. customusing a −78° C.
  3. additionAdd
  4. customapproximately 20 mL of the condensed liquid to the reaction mixture
  5. extractionAdd saturated, aqueous sodium hydrogencarbonate to the reaction mixture and extract product into the organics
  6. washWash
  7. customseparated organic layer with water
  8. dry with materialdry over magnesium sulfate

Sources & evidence

ORD record
ord-a4c7c1a46b6e468c80b6c02213c45a0e
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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