Sodium Carbonate → N-(2-methylbenzyloxycarbonyl)-tyrosinol

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Reaction Steps

In a mixture of 10 ml of water and 20 ml of ethyl acetate, 1.6 g of tyrosinol was dissolved. To the solution were added dropwise 2 g of 2-methylbenzyloxycarbonyl choride and 10 ml of an aqueous solution containing 1.3 g of sodium carbonate alternately with stirring while cooling with ice. After stirring for two hours at room temperature, the ethyl acetate layer was collected and washed with 5% hydrochloric acid and then with water. The layer was dried and concentrated to dryness. The residue was crystallized from ethyl acetate-petroleum ether to give 2.2 g of N-(2-methylbenzyloxycarbonyl)-tyrosinol with a mp. 78°-81° C in a yield of 70%. Analysis, calculated for C18H21O4N C 68.55, H 6.72. N 4.44, found C 68.88, H 6.84, N 4.42. According to the same procedure as used in Example 38, the following tyrosinol derivatives were prepared from the corresponding chlorides.

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