tert-Butanol → Tert-butyl acetoacetate

HRID 843311Notes

Reaction equation

HRID 843311 reaction equation
[C:1](OC)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[C:9]([OH:13])([CH3:12])([CH3:11])[CH3:10]>C1(C)C=CC=CC=1>[C:1]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 7757Methyl acetoacetate

Product 1

HCID 15538Tert-butyl acetoacetateYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1 equivalent of methyl acetoacetate, 1 equivalent of tertiary butyl alcohol and 100 mg of sulfated tin oxide catalyst prepared according to example 1, 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 t-butyl acetoacetate as a viscous colorless liquid in 50% 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-b8562b2281a641c6b3e5aa6cd92f3707
Source dataset
uspto-grants-2002_04
Patent number
US06376701B1

Reaction notes

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