Sodium Iodide → Ethyl 2-acetyl-4-oxovalerate

HRID 972951

Reaction equation

HRID 972951 reaction equation
[Na][CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[I-].[Na+].Cl[CH2:14][C:15](=[O:17])[CH3:16]>CC(C)=O>[C:5]([CH:4]([CH2:14][C:15](=[O:17])[CH3:16])[C:3](=[O:10])[CH3:2])([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 178472217HCID 178472217, compound

Product 1

HCID 3084847Ethyl 2-acetyl-4-oxovalerate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred and refluxing solution of ethyl sodioacetoacetate (0.5 mole, 78g.) and sodium iodide (1g.) in dry acetone (250 ml.) was added chloroactone (0.54 mol. 50g.) over a period of ten minutes. After one hour the acetone was distilled from the reaction mixture and the residue was diluted with 400 ml. water. The preciptated oil was extracted with ether and the ether removed to yield the intermediate 3-carbethoxy-2,5-hexanedione (75g.). The intermediate (26.4g.) was cyclized by heating under reflux over 5 g. anhydrous oxalic acid for 11/4 hours. The crude ester was saponified by heating under reflux for 45 minutes with potassium hydroxide (26g.) in methanol (200 ml.). The methanol was removed, the residue dissolved in water and the solution acidified to yield 2,5-dimethyl-3-furoic acid (18g.), m.p. 130°-133°.

Workup

  1. distillationAfter one hour the acetone was distilled from the reaction mixture
  2. additionthe residue was diluted with 400 ml
  3. extractionThe preciptated oil was extracted with ether
  4. customthe ether removed

Sources & evidence

ORD record
ord-e40474806ffd4df6884a91ddd2d51bc8
Source dataset
uspto-grants-1977_10
Patent number
US04054585

Linked notes

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