ChemicalBook CAS DataBase List 2-hydroxy-4-Methoxytoluene

2-hydroxy-4-Methoxytoluene synthesis

10synthesis methods

Product Name:2-hydroxy-4-Methoxytoluene
CAS Number:20734-74-1
Molecular formula:C8H10O2
Molecular Weight:138.16

673-22-3

20734-74-1

Example 84 Steps for the synthesis of ethyl 3-[4-(5-hydroxy-2-methylphenoxy)-2-methylphenyl]-propionate: Step A Preparation of 5-methoxy-2-methylphenol A solution of 2-hydroxy-4-methoxybenzaldehyde (5.00 g, 32.86 mmol), carbon-loaded palladium (10%, 3.50 g, 3.28 mmol) in ethanol (32 mL), and acetic acid (3 mL) was placed in a reactor and the reaction mixture was stirred at 60 psi hydrogen pressure. After overnight reaction, the mixture was filtered through a diatomaceous earth pad and washed with methanol. The filtrate was concentrated under reduced pressure and the resulting crude product was purified by fast column chromatography with hexane:ethyl acetate (2:1) as eluent to give 5-methoxy-2-methylphenol (3.96 g, 87% yield). Thin layer chromatography (TLC) Rf = 0.58 (unfolding agent: hexane:ethyl acetate 2:1).1H NMR (300MHz, CDCl3) δ: 2.18 (s, 3H), 3.75 (s, 3H), 6.42 (m, 2H), 7.00 (d, 1H, J = 8.9Hz).

673-22-3 Synthesis

673-22-3
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$5.00/1g

20734-74-1
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$13.00/100mg

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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50868-72-9 Synthesis