Methyl acetoacetate → 3-Phenylpropyl acetoacetate

HRID 843312Notes

Reaction equation

HRID 843312 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[C:9]1([CH2:15][CH2:16]CO)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[C:1]([O:7][CH2:8][CH2:16][CH2:15][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Participants

4

Reactant 2

HCID 7757Methyl acetoacetateHCID 31234Benzenepropanol

Product 1

HCID 110749123-Phenylpropyl acetoacetateYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1 equivalent of methyl acetoacetate, 1 equivalent of 3-phenylpropyl alcohol and 100 mg of sulfated tin oxide catalyst 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 3-phenylpropyl acetoacetate as a viscous colorless liquid in 97% yield.

Workup

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

Sources & evidence

ORD record
ord-9626877bf5294ba0867070b393af974c
Source dataset
uspto-grants-2002_04
Patent number
US06376701B1

Reaction notes

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