Acetone → HCID 70390697, compound

HRID 972954Notes

Reaction equation

HRID 972954 reaction equation
[Na]C[C:3](=O)[CH2:4][C:5]([O:7]CC)=[O:6].[I-].[Na+].Cl[CH:14]([CH3:18])[C:15](=[O:17])[CH3:16].[CH3:19]C(C)=O>>[CH3:3][C:4]1([C:5]([OH:7])=[O:6])[CH2:19][C:14]([CH3:18])=[C:15]([CH3:16])[O:17]1

Participants

5

Reactant 4

HCID 180AcetoneHCID 5238Sodium IodideHCID 200263-Chloro-2-butanoneHCID 178472217HCID 178472217, compound

Product 1

HCID 70390697HCID 70390697, compoundYield 76%

Procedure

To a stirred and refluxing solution of ethyl sodioacetoacetate (153 g.), sodium iodide (2 g.) and dry acetone (500 ml.) was added 3-chloro-2-butanone (1.1 mol., 117 g.) and the refluxing and stirring continued for 11/2 hours. The precipitated sodium chloride was filtered off from the reaction mixture and the acetone was removed from the filtrate. To the residue, water was added and the oily intermediate extracted with benzene. The benzene solution was treated with p-toluenesulfonic acid (0.5g.) and heated under reflux collecting the water of cyclization-dehydration in a Dean-Stark trap. After the reaction was completed (2-4 hours) the benzene was removed and the residual ester was saponified as in example 18 to give 117 g. (yield 76%) of 2,4,5-trimethylfuroic acid.

Workup

  1. stirringthe refluxing and stirring
  2. custom2 hours
  3. filtrationThe precipitated sodium chloride was filtered off from the reaction mixture
  4. customthe acetone was removed from the filtrate
  5. additionTo the residue, water was added
  6. extractionthe oily intermediate extracted with benzene
  7. additionThe benzene solution was treated with p-toluenesulfonic acid (0.5g.)
  8. temperatureheated
  9. temperatureunder reflux
  10. customcollecting the water of cyclization-dehydration in a Dean-Stark trap
  11. custom(2-4 hours)
  12. customwas removed
  13. customto give 117 g

Sources & evidence

ORD record
ord-6b53738b69a3446fbb3d69eee8c4c2d8
Source dataset
uspto-grants-1977_10
Patent number
US04054585

Reaction notes

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