Methyl acetoacetate → Acetoacetic acid, cyclohexyl ester

HRID 843310Notes

Reaction equation

HRID 843310 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[CH:9]1(O)[CH2:14][CH2:13]C[CH2:11][CH2:10]1>C1(C)C=CC=CC=1>[C:1]([O:7][CH:8]1[CH2:13][CH2:14][CH2:9][CH2:10][CH2:11]1)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Participants

4

Reactant 2

HCID 7757Methyl acetoacetateHCID 7966Cyclohexanol

Product 1

HCID 23376Acetoacetic acid, cyclohexyl esterYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1 equivalent of methyl acetoacetate, 1 equivalent of cyclohexanol 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 cyclohexyl acetoacetate as a viscous colorless liquid in 84% 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-8f423f0005ef410591af9427ab311bab
Source dataset
uspto-grants-2002_04
Patent number
US06376701B1

Reaction notes

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