ChemicalBook CAS DataBase List 1-(2-hydroxy-3-methoxy-phenyl)ethanone

1-(2-hydroxy-3-methoxy-phenyl)ethanone synthesis

14synthesis methods

Product Name:1-(2-hydroxy-3-methoxy-phenyl)ethanone
CAS Number:703-98-0
Molecular formula:C9H10O3
Molecular Weight:166.17

Preparation from 2,3-dimethoxybenzonitrile and methyl-magnesium iodide in refluxing ethyl ether (Grignard reaction) (75%).

Ethanone, 1-[3-methoxy-2-(phenylmethoxy)phenyl]-

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Yield: 89%

Reaction Conditions:

with hydrogenchloride;palladium on activated charcoal;hydrogen in methanol;water at 20; for 24 h;

Steps:

E E. 1-(2-Hydroxy-3-methoxyphenyl)ethan-1-one.
To a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen,was placed a solution of 1-[2-(benzyloxy)-3-methoxyphenyljethan-1-one (3 g,11.71 mmol,as prepared in the previous step) in MeOH (20 mL ) then conc. HC1 (0.1 mL) and Pd on carbon (300 mg) were added. The reaction was degassed and back-filled with H2 and stirred for 24 h at rt. The H2 was purged then the solids were removed by filtration. The filtrate was concentrated under reduced pressure affording 1.73 g (89%) of the title compound as a yellow solid. Mass Spectrum(LCMS,ESI pos): Calcd. for C9H11O3: 167.1 (M+H); Found: 167.1. 1H NMR (300 MHz,CDCl3): ö 12.58 (s,1H ),7.35 (d,J 8.2 Hz,1H ),7.07 (d,J= 7.9 Hz,1H ),6.86 (t,J= 8.1H z,1H ),3.91 (s,3H),2.65 (s,3H).

References:

PROTEOSTASIS THERAPEUTICS, INC.;MUNOZ, Benito;BASTOS, Cecilia, M.;PARKS, Daniel;KOMBO, David WO2017/62581, 2017, A1 Location in patent:Paragraph 0287

38480-94-3 Synthesis