Hydrochloric Acid → Ethyl pivaloylacetate

HRID 437478Notes

Reaction equation

HRID 437478 reaction equation
[C:1](=[O:8])([O:5][CH2:6][CH3:7])OCC.CN(C)P(=O)(N(C)C)N(C)C.[CH3:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23].Cl>O>[CH2:6]([O:5][C:1](=[O:8])[CH2:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6416PinacoloneHCID 7766Diethyl CarbonateHCID 12679Hexamethylphosphoramide

Product 1

HCID 86950Ethyl pivaloylacetateYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

250 g of potassium-tert.-butylate were suspended in a solution of 480 cc of diethyl carbonate and 100 cc of hexamethyl phosphoric acid triamide, followed by the gradual dropwise addition of 100 g pinacolone at 45° C/normal pressure. On completion of the addition, the mixture was stirred for 1 hour at 45° C and, after cooling, alcohol, water and finally hydrochloric acid carefully added one after the other to the reaction mixture. The reaction mixture was then treated and purified in the same way as described in 1 above. The yield was 67% of pivaloyl acetic acid ethyl ester.

Workup

  1. additionOn completion of the addition
  2. temperatureafter cooling
  3. additionThe reaction mixture was then treated
  4. custompurified in the same way

Sources & evidence

ORD record
ord-e8ea6bf62bc242d89cd654d51e7c2530
Source dataset
uspto-grants-1977_06
Patent number
US04031130

Reaction notes

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