Piperonal → 1,2-Bis(1,3-benzodioxol-5-yl)-2-hydroxyethanone

HRID 2109646Notes

Reaction equation

HRID 2109646 reaction equation
[CH:1]1[C:6]([CH:7]=[O:8])=[CH:5][C:4]2[O:9][CH2:10][O:11][C:3]=2[CH:2]=1.[C-]#N.[K+]>C(O)C.O>[CH2:10]1[O:11][C:3]2[CH:2]=[CH:1][C:6]([C:7]([CH:7]([C:6]3[CH:1]=[CH:2][C:3]4[O:11][CH2:10][O:9][C:4]=4[CH:5]=3)[OH:8])=[O:8])=[CH:5][C:4]=2[O:9]1

Participants

5

Reactant 2

HCID 8438PiperonalHCID 9032Potassium Cyanide

Product 1

HCID 977861,2-Bis(1,3-benzodioxol-5-yl)-2-hydroxyethanone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of piperonal (5 g) in ethanol (6.5 ml) was treated with a solution of potassium cyanide (0.5 g) in water (5 ml), then refluxed for 5 h. The resultant precipitate was filtered off, washed with water then crystallized from ethanol to give DC-0001B (2.24 g, 45%) as an off white crystalline solid.

Workup

  1. temperaturerefluxed for 5 h
  2. filtrationThe resultant precipitate was filtered off
  3. washwashed with water
  4. customthen crystallized from ethanol
  5. customto give DC-0001B (2.24 g, 45%) as an off white crystalline solid

Sources & evidence

ORD record
ord-cd02ac5abc92465faa9318ef30d4bcd8
Source dataset
uspto-grants-2009_04
Patent number
US07514583B2

Reaction notes

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