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2-{[4-(Hydroxymethyl)phenyl]methyl}isoindole-1,3-dione synthesis

3synthesis methods
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Yield:439691-95-9 93%

Reaction Conditions:

18-crown-6 ether in acetonitrile at 50; for 18 h;

Steps:

1

A mixture of 4-(chloromethyl)benzyl alcohol (0.839 g, 5.36 mmol), potassium phthalimide (1.41 g, 7.61 mmol), and 1,4,7, 10,13, 16-hexaoxacyclooctadecane (0.20 g, 0.76 mmol) in acetonitrile (10.0 mL, 191 mmol) was heated at 50 0C. After 18 h, the reaction mixture was filtered, washing with ethyl acetate. The filtrate was concentrated onto Celite, and the residue was purified via automated flash chromatography (40 g SiO2, hexanes to ethyl acetate) to afford the product as a white powder (1.33 g, 93%).LCMS Rt= 1.47 min MS m/z 268 [MH]+

References:

WO2010/33824,2010,A1 Location in patent:Page/Page column 40