Ethanol → Ethyl pivaloylacetate

HRID 437477Notes

Reaction equation

HRID 437477 reaction equation
[CH3:1][C:2](=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4].[C:8](=O)([O:12]CC)[O:9][CH2:10][CH3:11].CN(C)P(=O)(N(C)C)N(C)C.C(O)C>C1C=CC=CC=1>[CH2:10]([O:9][C:8](=[O:12])[CH2:1][C:2](=[O:7])[C:3]([CH3:6])([CH3:5])[CH3:4])[CH3:11]

Participants

6

Reactant 4

HCID 702EthanolHCID 6416PinacoloneHCID 7766Diethyl CarbonateHCID 12679Hexamethylphosphoramide

Product 1

HCID 86950Ethyl pivaloylacetateYield 54%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

A solution of 100 g of pinacolone in 500 cc of benzene was added dropwise over a period of 4 hours at 50° C/150 Torr to a solution of 500 cc of benzene, 900 cc of diethyl carbonate, 125 g of potassium-tert.-butylate and 200 cc of hexamethyl phosphoric acid triamide, and benzene and ethanol slowly distilled off. After the ketone had been added, another 500 cc of benzene were added dropwise. The total reaction time was 9 hours. The reaction mixture was then treated and distilled in the same way as described in 1 above. The yield was 54% of pivaloyl acetic acid ethyl ester.

Workup

  1. distillationslowly distilled off
  2. additionAfter the ketone had been added
  3. additionanother 500 cc of benzene were added dropwise
  4. additionThe reaction mixture was then treated
  5. distillationdistilled in the same way

Sources & evidence

ORD record
ord-2fe1987587e44feebad2573cbc677d29
Source dataset
uspto-grants-1977_06
Patent number
US04031130

Reaction notes

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