2-Methyl-1,3-cyclohexanedione → 5-Oxoheptanoic acid

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Reaction Steps

1-Bromo-5-methoxyheptane (Compound XX) is a reagent used for preparing preferred compounds X and XX. Compound XX is prepared in accordance with Reaction Scheme 3, starting from commercially available 2-methyl-1,3-cyclohexanedione. Thus, with reference to Reaction Scheme 3, 2-methyl-1,3-cyclohexanedione is reacted with base (Ba(OH)2) to yield 5-oxoheptanoic acid (Compound XXI). The oxo function of 5-oxoheptanoic acid (Compound XXI) is thereafter reduced, and the resulting hydroxy group, as well as the carboxylate function, are methylated to give methyl 5-methoxyheptanoate (Compound XXII). The carboxylate group of the latter is reduced (LiAlH4) to give 5-methoxy-1-heptanol (Compound XXIII), which is thereafter reacted with carbontetrabromide to yield 1-bromo-5-methoxyheptane (compound XX). ##STR6##

Provenance & Evidence