Quinone → 3-(3-Chlorophenyl)-7-methoxyisochromen-1-one

HRID 602278Notes

Reaction equation

HRID 602278 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][CH:7]=1.C1(=O)C=CC(=O)C=C1.[OH-].[Na+]>C1COCC1.CC#N.CC#N.Cl[Pd]Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:13][C:12](=[O:14])[C:11]3[C:10]([CH:9]=2)=[CH:18][CH:17]=[C:16]([O:19][CH3:20])[CH:15]=3)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 4650QuinoneHCID 14798Sodium HydroxideHCID 59684233(E)-2-[2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid

Product 1

HCID 596842713-(3-Chlorophenyl)-7-methoxyisochromen-1-oneYield 74%

Reagents, catalysts & solvents 2

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-2-[2-(3-chlorophenyl)vinyl]-5-methoxybenzoic acid (15.00 g, 51.95 mmol) in anhydrous THF (520 mL) was sparged with argon for 5 min. p-Benzoquinone (6.18 g, 57.20 mmol) was added followed by bis(acetonitrile)dichloropalladium(II) (674 mg, 2.60 mmol) and the resultant mixture stirred at ambient temperature for 17 h. 1 N NaOH (aq.) (375 mL) was added and the resultant brown solid washed with chloroform (4×200 mL) to provide 3-(3-chlorophenyl)-7-methoxyisochromen-1-one (10.96 g, 38.23 mmol, 74%) as pale yellow solid.

Workup

  1. additionwas added
  2. washthe resultant brown solid washed with chloroform (4×200 mL)

Sources & evidence

ORD record
ord-d6484199e0d94c5099bbae30993e39e8
Source dataset
uspto-grants-2011_03
Patent number
US07906504B2

Reaction notes

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