Acetic Acid → 1,3-Butanedione, 1-(2-furanyl)-

HRID 371090

Reaction equation

HRID 371090 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8]C)=O.[CH3:10][C:11]([CH3:13])=[O:12].CC(C)([O-])C.[K+].C(O)(=O)C>C1(C)C=CC=CC=1.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:8])[CH2:10][C:11](=[O:12])[CH3:13]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 11902Methyl 2-furoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 121681,3-Butanedione, 1-(2-furanyl)-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of methyl 2-furoate (23 g, 0.18 mole) and acetone (10.6 g, 0.18 mole) was slowly added to a stirred suspension of potassium tert-butoxide (41 g, 0.36 mole) in anhydrous toluene (300 ml) at 0° C. Upon standing overnight at room temperature, glacial acetic acid (22 ml, 0.36 mole) and then water (100 ml) were added. The organic layer was separated, combined with an ether extract of the aqueous phase, washed with water, dried, and distilled to give 1-(2-furyl)-1,3-dioxobutane: b.p. 66°-70° C./0.1 mm (18.5 g).

Workup

  1. customThe organic layer was separated
  2. extractionextract of the aqueous phase
  3. washwashed with water
  4. customdried
  5. distillationdistilled

Sources & evidence

ORD record
ord-7805c0baa15549b38d0828aa8c242789
Source dataset
uspto-grants-1985_07
Patent number
US04529733

Linked notes

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