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ChemicalBook CAS DataBase List 2-(3-hydroxycyclohexyl)isoindoline-1,3-dione

2-(3-hydroxycyclohexyl)isoindoline-1,3-dione synthesis

4synthesis methods
2-(2-bromo-3-hydroxy-cyclohexyl)-isoindole-1,3-dione

1403864-57-2
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Yield:202479-02-5 81%

Reaction Conditions:

with methanol;tri-n-butyl-tin hydride;2,2'-azobis(isobutyronitrile) in toluene at 80; for 64 h;

Steps:

18.C

Tri-n-butyltin hydride (430 g, 1.48 mol) was added to a stirred solution of 2-(2-bromo-3-hydroxy-cyclohexyl)- isoindole-l ,3-dione (400 g, 1.23 mol) and 2,2'-azobis(2-methylpropionitrile) (20 g) in toluene (4000 mL) and methanol (400 mL) and the reaction mixture was stirred at 80 °C for 64 h. The reaction mixture was concentrated to give the crude product. The crude product was washed with petroleum ether and ethyl acetate (1 : 1) to give 2-(3-hydroxy- cyclohexyl)-isoindole-l ,3-dione (240 g, 0.98 mol) as a white solid. 1H NMR (CD3OD, 400 MHz): δ ppm 7.82 (m, 4H), 4.16 (m, 1H), 3.63 (m, 1H), 2.13 (m, 2H), 1.98 (d, 2H), 1.89 (m, 1H), 1.68 (t, 1H), 1.46 (m, lH),1.31(m, 1H).

References:

WO2012/145569,2012,A1 Location in patent:Page/Page column 119