1,3-Dihydroisobenzofuran → Phthalaldehyde

HRID 1532477Notes

Reaction equation

HRID 1532477 reaction equation
C1OCC2C1=CC=CC=2.ON1[C:15](=[O:16])[C:14]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]2[C:12]1=[O:21]>C(#N)C>[CH:12](=[O:21])[C:13]1[C:14](=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH:15]=[O:16]

Participants

4

Reactant 2

HCID 103271,3-Dihydroisobenzofuran2×HCID 10665N-Hydroxyphthalimide

Product 1

HCID 4807PhthalaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 10 mmol of phthalan (isocoumaran), 1 mmol of N-hydroxyphthalimide, and 5 ml of acetonitrile was introduced 60 mmol of nitrogenmonoxide, and the resultant mixture was stirred at 60° C. for 8 hours. Isolation of products in the reaction mixture by column chromatography on a silica gel revealed that phthalan was converted, at a rate of 95%, into phthalaldehyde (yield: 88%) and 1-hydroxyphthalan (yield: 3%).

Workup

  1. additionwas introduced 60 mmol of nitrogenmonoxide

Sources & evidence

ORD record
ord-4d0eb9e57e2a42e2bd18858b5887d6c6
Source dataset
uspto-grants-2001_03
Patent number
US06201156B1

Reaction notes

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