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ChemicalBook CAS DataBase List 1-(3,4-dihydroxyphenyl)cyclopropanecarbonitrile
952664-49-2

1-(3,4-dihydroxyphenyl)cyclopropanecarbonitrile synthesis

2synthesis methods
Cyclopropanecarbonitrile, 1-[3,4-bis(phenylmethoxy)phenyl]-

952664-48-1
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1-(3,4-dihydroxyphenyl)cyclopropanecarbonitrile

952664-49-2
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Yield:952664-49-2 92%

Reaction Conditions:

with hydrogen;palladium on activated charcoal in methanol at 20; under 760.051 Torr; for 4 h;

Steps:

4

To a solution of 1-(3,4-bis-benzyloxy-phenyl)-cyclopropanecarbonitrile (10 g, 28 mmol) in MeOH (50 mL) was added Pd/C (0.5 g) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature for 4 h. The catalyst was filtered off through a celite pad and the filtrate was evaporated under vacuum to give 1-(3,4-dihydroxy-phenyl)-cyclopropanecarbonitrile (4.5 g, 92%). 1H NMR (DMSO 400 MHz) δ 9.06 (br s, 2H), 6.67-6.71 (m, 2H), 6.54 (dd, J=2.4, 8.4 Hz, 1H), 1.60-1.57 (m, 2H), 1.30-1.27 (m, 2H).

References:

US2007/244159,2007,A1 Location in patent:Page/Page column 81