Toluene → 5-Methylhexanoic acid

HRID 2374722Notes

Reaction equation

HRID 2374722 reaction equation
[C:1]([O:4]CC)(=[O:3])[CH3:2].[C:7]1([CH3:13])[CH:12]=CC=[CH:9][CH:8]=1>>[CH3:12][CH:7]([CH3:13])[CH2:8][CH2:9][CH2:2][C:1]([OH:4])=[O:3]

Participants

3

Reactant 2

HCID 1140TolueneHCID 8857Ethyl Acetate

Product 1

HCID 123445-Methylhexanoic acid

Conditions

Temperature
250 °C

Procedure

The crude ester prepared in example 1, is added to a mixture of ethyl acetate and toluene, and heated to 80° C. (range 400 to 100° C.) until dissolution. The solution is cooled to 2° C. (range 0° to 20° C.) to get a yellowish solid of (S)-3-(1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)carbonyl)methyl)-5-methylhexanoic acid (Fenchyl ester), which is filtered from the mixture.

Workup

  1. dissolutionuntil dissolution
  2. temperatureThe solution is cooled to 2° C. (range 0° to 20° C.)

Sources & evidence

ORD record
ord-cfb8df6c0c594fe0bff75ea8e7f4a6d7
Source dataset
uspto-grants-2008_12
Patent number
US07462738B2

Reaction notes

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