Process for production of dihydromyrcenol and dihydromyrcenyl acetate

摘要

Described is a novel process for preparing dihydromyrcenol defined according to the structure:or the acetate thereof comprising the steps of:(i) hydrogenating a-pinene to form a-pinane;(ii) pyrolizing the resulting a-pinane to form a mixture of hydrocarbons including dihydromycene (or, in the atterna- tive, forming substantially the same mixture of hydrocarbons by other well known means);(iii) reacting the resulting pinane pyrolyzate or like mixture with hydrogen chloride gas in the presence of an acid catalyst, e.g., Lewis acid or protonic acid, to form a mixture of tertiary chlorides; then(iv) reacting the mixture of tertiary chlorides with water or acetic acid in the presence of a hydroxylation catalyst defined according to the formula:wherein M represents an element selected from the group consisting of Zn, Ca, Mg, Mn and Co; wherein X represents 0 or an anion, e.g., halide hydroxide, carbonate, bicarbonate, phosphate, monobasic acid phosphate or dibasic acid phosphate; and wherein p represents an integer of 1 or 3 and q represents an integer of 1 or 2, with the provisos that when X is a trivalent anion, then p is 3 and q is 2 and when X is a divalent anion or is 0, then p is 1 and q is 1 and when X is a monovalent anion then p is 1 and q is 2; and(v) recovering the dihydromyrcenol or acetate thereof from the reaction product where the dihydromyrcenol or acetate thereof is produced in relatively high yields.