Chloroacetone → HCID 15310185, compound

HRID 376814Notes

Reaction equation

HRID 376814 reaction equation
[CH:1]([C:3]1[CH:10]=[C:7]([CH:8]=O)[C:6]([OH:11])=[CH:5][CH:4]=1)=[O:2].Cl[CH2:13][C:14](=[O:16])[CH3:15].C(N(C(C)C)CC)(C)C>C(O)C>[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:13]([C:14](=[O:16])[CH3:15])=[CH:8][C:7]=2[CH:10]=1)=[O:2]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 81531DiisopropylethylamineHCID 1651064-Hydroxyisophthalaldehyde

Product 1

HCID 15310185HCID 15310185, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

About 5.0 g (1.0 equivalent) of 5-formylsalicylaldehyde was dissolved in about 15 ml of ethanol, and about 3.25 g (about 1.05 equivalents) of monochloroacetone was added thereto. Then, about 8.7 ml (about 1.50 equivalents) of diisopropylethylamine was added thereto at room temperature. The mixture was heated while being stirred for about 5 hours, and maintaining the reaction temperature at about 60° C. to 70° C. After confirming the completion of the reaction by TLC, the mixture was allowed to cool down. The produced solid matter was separated by filtering, and washed with ethanol. Then, the solid matter was recrystallized from ethanol so as to obtain about 5.8 g of the target 5-formyl-2-acetylbenzo[b]furan in the form of white crystal (yield: about 92.6%).

Workup

  1. customat room temperature
  2. temperatureThe mixture was heated
  3. temperaturemaintaining the reaction temperature at about 60° C. to 70° C
  4. customthe completion of the reaction by TLC
  5. temperatureto cool down
  6. customThe produced solid matter was separated
  7. filtrationby filtering
  8. washwashed with ethanol
  9. customThen, the solid matter was recrystallized from ethanol so as

Sources & evidence

ORD record
ord-08cddad77a75474482546b7136fe9150
Source dataset
uspto-grants-2000_02
Patent number
US06022655

Reaction notes

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