Potassium Iodide → Diethyl 2-acetyl-3-methylbutanedioate

HRID 1701585Notes

Reaction equation

HRID 1701585 reaction equation
Cl[CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][C:11]([CH3:13])=[O:12].[Cl-].C([N+](C(=O)CCCCCCC)(C(=O)CCCCCCC)C)(=O)CCCCCCC.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[C:11]([CH:10]([CH:2]([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:9]([O:15][CH2:16][CH3:17])=[O:14])(=[O:12])[CH3:13]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 8868Ethyl AcetoacetateHCID 10807Ethyl 2-chloropropionateHCID 11430Potassium CarbonateHCID 14567419HCID 14567419, compound

Product 1

HCID 12354293Diethyl 2-acetyl-3-methylbutanedioate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Process according to claim 4 wherein ethyl chloropropionate is reacted with ethyl acetoacetate in a toluene mixture containing tricaprylyl methylammonium chloride as phase transfer agent, potassium iodide as iodide ion source, potassium carbonate, milled to below about 80 mesh as deprotonating base at 75° to 80° C. for a time sufficient to form diethyl α-acetyl-α'-methylsuccinate.

Workup

  1. custommilled to below about 80 mesh
  2. customat 75° to 80° C.

Sources & evidence

ORD record
ord-1e0d5db8f1814678b050de04cc5a8bef
Source dataset
uspto-grants-1980_03
Patent number
US04194053

Reaction notes

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