1,3-Dihydroisobenzofuran → Phthalaldehyde

HRID 1532473Notes

Reaction equation

HRID 1532473 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].[C:15]1([C:14]2[C:13](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:12][O:21]1)=[O:16]

Participants

5

Reactant 2

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

Product 2

HCID 4807PhthalaldehydeYield 80%HCID 6885PhthalideYield 7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 10 mmol of phthalan (isocoumaran), 1 mmol of N-hydroxyphthalimide (NHPI), and 5 ml of acetonitrile was stirred at 60° C. under a nitrogen monoxide atmosphere (1 atm) for 6 hours. Gas chromatographic analysis of products in the reaction mixture revealed that phthalan was converted, at a rate of 90%, into phthalaldehyde (yield: 80%), and phthalide (1-phthalanone) (yield: 7%).

Sources & evidence

ORD record
ord-04915df794fa4210b0f43794149e6178
Source dataset
uspto-grants-2001_03
Patent number
US06201156B1

Reaction notes

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