Salicylaldehyde → Methanone, 2-benzofuranylphenyl-

HRID 1289027Notes

Reaction equation

HRID 1289027 reaction equation
[CH:1](=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[OH-].[K+].[CH2:12](Cl)[C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]>C(O)C>[C:13]([C:12]1[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[CH:1]=1)(=[O:14])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 107572-ChloroacetophenoneHCID 14797Potassium Hydroxide2×

Product 1

HCID 95808Methanone, 2-benzofuranylphenyl-Yield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

24.4 g of salicylaldehyde and 300 ml of ethanol are mixed with 11.6 g of potassium hydroxide. The resulting suspension is agitated at room temperature until the potassium hydroxide is completely dissolved. Subsequently, 31 g of phenacyl chloride are added in portions to the solution, and the batch is heated under stirring in a reflux condenser for 2 hours. The crystals precipitated while cooling down to room temperature are filtered by suction, washed with water, and recrystallized from methanol. Another fraction may be obtained by evaporating the mother liquor. Yield: 70%, colourless crystals.

Workup

  1. dissolutionis completely dissolved
  2. temperaturethe batch is heated
  3. customThe crystals precipitated
  4. filtrationare filtered by suction
  5. washwashed with water
  6. customrecrystallized from methanol
  7. customAnother fraction may be obtained
  8. customby evaporating the mother liquor

Sources & evidence

ORD record
ord-5a78c261060a46be939ca67b6733e6c6
Source dataset
uspto-grants-1998_05
Patent number
US05747508

Reaction notes

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