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36.1.6.3.1 Variation 1: Addition of Organomagnesium Compounds

DOI: 10.1055/sos-SD-036-00173

Grosjean, C.; Whiting, A.Science of Synthesis, (200836261.

Aside from the patents issued by Bayer in the early 20th century,[‌23‌,‌24‌] preparation of tertiary alcohols from carboxylic acids has not been extensively described. Of note, however, is a general method published by Huston and Bailey,[‌25‌] in which 1 mole of acid in diethyl ether is added slowly to the Grignard reagent (3.3mol) and the mixture is refluxed on a water bath for 2hours. The authors note that adding the acid in benzene (200mL per mole of acid), distilling off the diethyl ether until the temperature reaches 83°C, and then refluxing for 2hours all increase the yield of tertiary alcohol produced. No workup procedure was given.

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