ETHER, p-MENTH-8-EN-l-YL METHYL

Ether, bis(2-methoxyethyl), 61, 103 Ether, dichloromethyl methyl, 61, 1 ETHER, p-MENTH-8-EN-l-YL METHYL, cis-, 61, 112... 

PHOTOPROTONATION OF CYCLOALKENES LIMONENE TO p-MENTH-8-EN-l-YL METHYL ETHER... 

The solution is poured into 900 mL of 5% aqueous sodium hydroxide solution containing 125 g of sodium chloride, and the mixture is extracted with two 100-mL portions of ether. The ether layers are combined, washed with 50 mL of saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The drying agent is removed by filtration and the filtrate is concentrated with a Buchi rotary evaporator. After a preliminary distillation to separate the product from a small amount of nonvolatile material, the liquid is distilled at reduced pressure through a Teflon spinning band column (47 cm x 7 mm). The material that distills at 90-95°C (10 mm) is collected to give 12.8-13.2 g (52-53%) of a mixture of cis- and rran -p-menth-S-en-l-yl methyl ether (Notes 8-10). 

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