tert-Butanol → Tert-butyl 3-cyclopropyl-3-oxopropanoate

HRID 342959Notes

Reaction equation

HRID 342959 reaction equation
[CH:1]1([C:4]([CH:6]2[C:11](=[O:12])[O:10][C:9]([CH3:14])([CH3:13])OC2=O)=[O:5])[CH2:3][CH2:2]1.[C:16](O)(C)(C)C>C1(C)C=CC=CC=1>[CH:1]1([C:4](=[O:5])[CH2:6][C:11]([O:10][C:9]([CH3:13])([CH3:14])[CH3:16])=[O:12])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 545285405-(Cyclopropylcarbonyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 11126948Tert-butyl 3-cyclopropyl-3-oxopropanoateYield 97.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-cyclopropylcarbonyl-2,2-dimethyl-1,3-dioxan-4,6-dione (23.9 g) and t-butanol (25 g) in dry toluene (80 ml) was stirred and heated at 80° C. for 4 hours. The cooled mixture was washed with water (3×30 ml), dried (anhydrous sodium sulphate), treated with decolourizing charcoal and filtered. The filtrate was evaporated to dryness and the residue was distilled to give t-butyl 3-cyclopropyl-3-oxopropionate (20.2 g) as a clear oil bp 80°-84° C./8 mmHg.

Workup

  1. washThe cooled mixture was washed with water (3×30 ml)
  2. dry with materialdried (anhydrous sodium sulphate)
  3. additiontreated with decolourizing charcoal
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-6110e7ee188c4096a37e0a64e2584b51
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

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