Hydrochloric Acid → 1,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal

HRID 1003698Notes

Reaction equation

HRID 1003698 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][CH2:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18])C.Cl>O1CCCC1>[C:9]1(=[O:18])[N:8]([CH2:7][CH2:6][CH2:5][CH:4]=[O:3])[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 128051862-(4,4-Diethoxybutyl)isoindoline-1,3-dione

Product 1

HCID 771501,3-Dihydro-1,3-dioxo-2H-isoindole-2-butanal

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-phthalimidobutyraldehyde diethyl acetal (125 g, 0.43 mol) in a 1:1 mixture of tetrahydrofuran and 2N hydrochloric acid (800 ml) was heated at reflux for 0.75 h. The mixture was cooled, concentrated to 400 ml and extracted into dichloromethane (3×200 ml). Combined organics were dried (Na2SO4) and evaporated in vacuo to afford the title compound as a brown oil that solidified on standing (95 g, 100%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 0.75 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated to 400 ml
  5. extractionextracted into dichloromethane (3×200 ml)
  6. dry with materialCombined organics were dried (Na2SO4)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-1daafa01c81d4908bb62145a14c1f050
Source dataset
uspto-grants-2000_04
Patent number
US06046210

Reaction notes

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