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ChemicalBook CAS DataBase List 2-hydroxy-4-Methoxytoluene
20734-74-1

2-hydroxy-4-Methoxytoluene synthesis

10synthesis methods
-

Yield:20734-74-1 87%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in ethanol;acetic acid under 3102.97 Torr;

Steps:

84.A
Example 84 3- [4- (5-Hydroxy-2-methyl-phenoxy)-2-methyl-phenyl]-propionic acid ethyl ester Step A 5-Methoxy-2-methyl-phenol A solution of 2-hydroxy-4-methoxy-benzaldehyde (5.00 g, 32.86 mmol) and palladium under carbon (10 %) (3.50 g, 3.28 mmol) in ethanol (32 mL) and acetic acid (3 mL) is stirred under 60 psi of hydrogen. After stirring overnight, the mixture is filtered off through Celite and washed with methanol. The mixture is concentrated under reduced pressure, and purified by flash chromatography by eluting with hexane: ethyl acetate 2: 1 to afford the title compound (3.96 g, 87 %). Rf= 0.58 (hexane: ethyl acetate 2: 1). 8'H NMR (300 MHz, CDC13) : 2.18 (s, 3 H), 3.75 (s, 3 H), 6.42 (m, 2 H), 7.00 (d, 1 H, J= 8. 9 Hz).

References:

ELI LILLY AND COMPANY WO2005/37763, 2005, A1 Location in patent:Page/Page column 130-131

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