ChemicalBook CAS DataBase List 4-(2-AMINO-ETHYL)-2-METHOXY-PHENOL

4-(2-AMINO-ETHYL)-2-METHOXY-PHENOL synthesis

11synthesis methods

Product Name:4-(2-AMINO-ETHYL)-2-METHOXY-PHENOL
CAS Number:554-52-9
Molecular formula:C9H13NO2
Molecular Weight:167.21

Hydroxy(4-hydroxy-3-methoxyphenyl)acetonitrile

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Yield:554-52-9 86%

Reaction Conditions:

with sulfuric acid;hydrogen;5%-palladium/activated carbon in methanol at 20 - 25; under 3750.38 Torr; for 4.33333 h;

Steps:

19
Example 19: 4-aminoethyl-2-methoxy phenol (Compound of formula IV via intermediate IVA") To a 300ml pressure reactor was added 30ml methanol and 31. Ig of 98% sulphuric acid (1.41eq). A slurry of 3.8g 5% palladium on charcoal catalyst (0.004eq) in 10ml of methanol was added, followed by a 10ml methanol wash. With the reactor under 5 bar hydrogen pressure and while maintaining a temperature of 20-25 °C, lOOg of 40% vanillin cyanohydrin solution in methanol (leq vanillin cyanohydrin) was fed over 4 h, followed by a 15ml methanol wash. After 20 minutes stirring, the pressure was relieved and 75ml water added. This mixture was stirred at 45 ⁰C to dissolve the product and then the catalyst filtered off. The catalyst cake was washed with 3 x 25ml water and these washes combined with the mother liquor to give a product solution of 315g, containing 10.0% AE-phenol by HPLC (86% yield).

References:

SYNGENTA PARTICIPATIONS AG WO2007/20381, 2007, A2 Location in patent:Page/Page column 16; 30

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4468-59-1 Synthesis