Acetone → 1-(6-methyl-3,4-dihydro-2H-pyran-5-yl)ethan-1-one

HRID 1905413Notes

Reaction equation

HRID 1905413 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:16][C:17]([CH3:19])=O>>[C:4]([C:3]1[CH2:16][CH2:17][CH2:19][O:7][C:2]=1[CH3:1])(=[O:6])[CH3:5]

Participants

5

Reactant 4

HCID 180AcetoneHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 31261Acetylacetone

Product 1

HCID 130501371-(6-methyl-3,4-dihydro-2H-pyran-5-yl)ethan-1-one

Procedure

A mixture of 130.4 g. (1.3 moles) of 2,4-pentanedione, 251.9 g. (1.6 moles) of 1,3-bromochloropropane, 168 g. (1.2 moles) of anhydrous potassium carbonate, 1 g. of anhydrous sodium iodide and 250 ml. of dry acetone is refluxed for 20 hours, under exclusion of humidity, with stirring. After cooling the mixture is filtered, washed with four 150-ml. portions of dry acetone, the combined acetone extract is evaporated, and the residue is subjected to fractionated distillation in vacuum, on a Vigreux column.

Workup

  1. additionA mixture of 130.4 g
  2. temperatureAfter cooling the mixture
  3. filtrationis filtered
  4. washwashed with four 150-ml
  5. extractionportions of dry acetone, the combined acetone extract
  6. customis evaporated
  7. distillationthe residue is subjected to fractionated distillation in vacuum, on a Vigreux column

Sources & evidence

ORD record
ord-0cbee646f764447887e4926ad61faec7
Source dataset
uspto-grants-1989_06
Patent number
US04843080

Reaction notes

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