Hydroquinone → Ketoethyl methacrylate

Participants

Reaction Steps

In a 2 L four-necked flask, 180 g of potassium methacrylate (made by Wako Pure Chemical Industries Ltd., purity: 98.0%) was put, and 900 g of N,N-dimethylformamide was added thereto, and a stirrer, a thermometer and a Dimroth cooling tube were connected thereto. Then, 308 g of 2-bromo-1,1-diethoxyethane (made by ALDRICH Corporation, purity: 97%), 0.9 g of p-methoxyphenol and 1.32 g of tetramethylammonium iodide were added thereto, and the resulting mixture was allowed to react for 2 hours at 150° C. under stirring. The reaction mixture was cooled to room temperature, a precipitate was separated by filtration, and then N,N-dimethylformamide was distilled off, and the resulting product was distilled under reduced pressure to obtain 174 g of a reaction product (GC purity: 98.5%). From the thus obtained reaction product, 19 g was put into a 1 L four-necked flask subjected to replacement with nitrogen, stirred and dispersed into 430 mL of water, and 0.21 g of hydroquinone, 0.41 g of 1-phenyl-3-pyrazolidinone (made by Tokyo Kasei Kogyo Co., Ltd., purity: 98.0% or more) and 2.8 g of 85% phosphoric acid were added thereto, and the resulting mixture was allowed to react at 70 to 80° C. for 3 hours under stirring. The reaction mixture was cooled to room temperature, and neutralized using a 10% sodium hydrogen carbonate aqueous solution, and repeatedly extracted with diethyl ether. An organic layer was dried over magnesium sulfate, separated by filtration, and distilled under reduced pressure to give 5.6 g of 2-oxoethyl methacrylate (yield: 27.6% based on potassium methacrylate).

Provenance & Evidence