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

HRID 258178

Reaction equation

HRID 258178 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([O:9][CH3:10])[CH2:7][CH3:8].[CH3:11][CH:12]1[C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:13]1=[O:19]>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH:6]([O:9][CH3:10])[CH2:7][CH3:8].[O:18]=[C:17]([CH2:12][CH3:11])[CH2:16][CH2:15][CH2:14][C:13]([OH:19])=[O:9]

Participants

4

Reactant 2

HCID 709452-Methyl-1,3-cyclohexanedione2×HCID 197827511-Bromo-5-methoxyheptane3×

Product 2

HCID 52829795-Oxoheptanoic acidHCID 197827511-Bromo-5-methoxyheptane

Procedure

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##

Workup

  1. customused for preparing

Sources & evidence

ORD record
ord-a8379440f6564457abcc829a382af2dd
Source dataset
uspto-grants-1993_11
Patent number
US05264619

Linked notes

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