Methyl vinyl ketone → HCID 11817624, compound

HRID 274886Notes

Reaction equation

HRID 274886 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18](=[O:21])[CH:19]=[CH2:20]>CC(=O)CC>[C:18]([C:19]1[CH2:20][O:10][C:5]2[C:6]([CH:7]=1)=[CH:9][C:2]([Br:1])=[CH:3][CH:4]=2)(=[O:21])[CH3:17]

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 11430Potassium Carbonate2×HCID 728635-Bromosalicylaldehyde

Product 1

HCID 11817624HCID 11817624, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A heterogeneous solution of 100 g (497 mmol) of 5-bromo-2-hydroxybenzaldehyde and 13.8 g (10 mmol) of potassium carbonate (previously finely ground and dried at 90° C.) in 220 ml of butan-2-one is brought to reflux. A solution of 35.31 g (i.e. 42 ml, 497 mmol) of but-3-en-2-one in 40 ml of butan-2-one is then added dropwise over a period of from 15 to 20 minutes. After 4 hours' refluxing, 13.8 g (10 mmol) of potassium carbonate are added. The mixture is refluxed for 16 hours. When the reaction mixture has returned to room temperature, the solid is separated off by filtration and then washed with 2×50 ml of butan-2-one. The filtrate is then concentrated and the residue is purified by chromatography over a silica column (eluant: methylene chloride/cyclohexane, 1:1). Recrystallisation from diisopropyl ether yields 73 g of a yellowish solid.

Workup

  1. temperatureto reflux
  2. temperatureAfter 4 hours' refluxing
  3. temperatureThe mixture is refluxed for 16 hours
  4. customhas returned to room temperature
  5. customthe solid is separated off by filtration
  6. washwashed with 2×50 ml of butan-2-one
  7. concentrationThe filtrate is then concentrated
  8. customthe residue is purified by chromatography over a silica column (eluant: methylene chloride/cyclohexane, 1:1)
  9. customRecrystallisation from diisopropyl ether

Sources & evidence

ORD record
ord-91d3f411e94b4e5faec49f5c0bff891f
Source dataset
uspto-grants-1995_02
Patent number
US05391569

Reaction notes

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