Water → Tert.butyl 2-chloro-2,3-epoxy-3-isopropyl-butanoate

HRID 1657710Notes

Reaction equation

HRID 1657710 reaction equation
[CH:1]([C:4]([CH3:6])=[O:5])([CH3:3])[CH3:2].Cl[CH:8]([Cl:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].O>O1CCCC1>[Cl:16][C:8]1([O:5][C:4]1([CH:1]([CH3:3])[CH3:2])[CH3:6])[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 112513-Methyl-2-butanoneHCID 30164831,1-Dimethylethyl dichloroacetate

Product 1

HCID 21443884Tert.butyl 2-chloro-2,3-epoxy-3-isopropyl-butanoateYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 122 g of potassium tert.-butylate in 720 ml of tetrahydrofuran was added with stirring under an inert atmosphere at -20°C to a mixture of 95 g of methyl isopropyl ketone and 185 g of tert.-butyl dichloroacetate and the mixture was allowed to return to room temperature and was stirred for 2 hours. The mixture was poured into iced water and stirred after which the organic phase was removed, washed with aqueous sodium chloride solution and dried over magnesium sulfate. After passing the solution through vegetable black, the solution was concentrated to dryness to obtain 230.4 g of tert.-butyl 2-chloro-2,3-epoxy-3-isopropyl-butanoate in the form of a colorless liquid soluble in the usual organic solvents and insoluble in water.

Workup

  1. customto return to room temperature
  2. stirringstirred after which the organic phase
  3. customwas removed
  4. washwashed with aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationthe solution was concentrated to dryness

Sources & evidence

ORD record
ord-d362b21d111a47e2887c3edc9f081fe3
Source dataset
uspto-grants-1976_06
Patent number
US03962223

Reaction notes

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