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ChemicalBook CAS DataBase List carbamic acid, [(4-methoxyphenyl)methyl]-, ethyl ester

carbamic acid, [(4-methoxyphenyl)methyl]-, ethyl ester synthesis

9synthesis methods
-

Yield:35573-36-5 43.8%

Reaction Conditions:

with triethylamine in tetrahydrofuran;

Steps:

1.A Synthesis of Ethyl (4-methoxyphenylmethyl)carbamate as an Intermediate

Step A Synthesis of Ethyl (4-methoxyphenylmethyl)carbamate as an Intermediate A stirred solution of 6.0 mL (0.046 mole) of 4-methoxyphenylmethyl-amine and 6.5 mL (0.047 mole) of triethylamine in 200 mL of tetrahydrofuran was cooled to about 5° C., and a solution of 4.4 mL (0.046 mole) of ethyl chloroformate in 10 mL of tetrahydrofuran was added. Upon completion of the addition the reaction mixture was allowed to warm to ambient temperature, then was poured into a mixture of 200 mL of ice and 200 mL of an aqueous solution saturated with ammonium chloride. This mixture was extracted with 300 mL of diethyl ether, and the extract was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 4.2 grams (43.8% yield) of ethyl (4-methoxyphenylmethyl)-carbamate. The NMR spectrum was consistent with the proposed structure.

References:

US5780630,1998,A