Menthol → Butanoic acid, 3-oxo-, 5-methyl-2-(1-methylethyl)cyclohexyl ester

HRID 843309Notes

Reaction equation

HRID 843309 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH:9]1([CH3:19])[CH2:14]C[CH:12]([CH:15]([CH3:17])[CH3:16])[CH:11](O)[CH2:10]1>C1(C)C=CC=CC=1>[C:1]([O:7][CH:8]1[CH:12]([CH:15]([CH3:17])[CH3:16])[CH2:11][CH2:10][CH:9]([CH3:19])[CH2:14]1)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Participants

4

Reactant 2

HCID 1254MentholHCID 7757Methyl acetoacetate

Product 1

HCID 102565Butanoic acid, 3-oxo-, 5-methyl-2-(1-methylethyl)cyclohexyl esterYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1 equivalent of methyl acetoacetate, 1 equivalent of menthol and 100 mg of sulfated tin oxide catalyst prepared according to example 1 above, in 20 ml of toluene was heated to 110° C. in a two necked round bottom flask provided with a distillation condenser to remove methanol. The reaction was monitored by thin layer chromatography (TLC). After completion of the reaction (about 6 hours), the catalyst was filtered and the filtrate was concentrated and chromatographed on a silica gel column (95% petroleum ether and 5% ethyl acetate) to afford menthyl acetoacetate as a viscous colorless liquid in 91% yield.

Workup

  1. customprepared
  2. customprovided with a distillation condenser
  3. customto remove methanol
  4. customAfter completion of the reaction (about 6 hours)
  5. filtrationthe catalyst was filtered
  6. concentrationthe filtrate was concentrated
  7. customchromatographed on a silica gel column (95% petroleum ether and 5% ethyl acetate)

Sources & evidence

ORD record
ord-0813c3c554424470bf6c861d818781eb
Source dataset
uspto-grants-2002_04
Patent number
US06376701B1

Reaction notes

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