1,3-Dihydroisobenzofuran → Phthalaldehyde

HRID 1532476Notes

Reaction equation

HRID 1532476 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 1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 10 mmol of phthalan (isocoumaran), 1 mmol of N-hydroxyphthalimide, and 5 ml of acetonitrile was introduced 10 mmol of nitrogenmonoxide, and the resultantmixture 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 15%, into phthalaldehyde (yield: 1%), 1-hydroxyphthalan (yield: 3%), NHPI adduct (yield: 3%), and an acetamide compound (yield: 3%).

Workup

  1. additionwas introduced 10 mmol of nitrogenmonoxide

Sources & evidence

ORD record
ord-b493ce03193d43dfbb805c573957600f
Source dataset
uspto-grants-2001_03
Patent number
US06201156B1

Reaction notes

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