Piperonal → Piperonyl alcohol

HRID 2103740Notes

Reaction equation

HRID 2103740 reaction equation
[CH2:1]1[O:5][C:4]2[CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=[CH:9][C:3]=2[O:2]1.[H][H]>[Ni].C(O)CC>[CH2:10]([OH:11])[C:7]1[CH:8]=[CH:9][C:3]2[O:2][CH2:1][O:5][C:4]=2[CH:6]=1

Participants

5

Reactant 2

HCID 8438PiperonalHCID 178418361HCID 178418361, compound

Product 1

HCID 10322Piperonyl alcoholYield 30.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 10311-PropanolSolvent

Conditions

Temperature
90 °C

Procedure

In a 500-ml autoclave were placed 90 g (0.60 mol) of heliotropin, 270 ml of 1-propanol and 3 g of a Raney nickel catalyst (Raney-Ni). Hydrogen gas was filled therein up to 4 MPa. The autoclave contents were stirred at 90° C. for about 10 hours. The reaction mixture was filtered and the filtrate was concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain 27.6 g of piperonyl alcohol as white crystals (yield: 30.3%, G.C. purity: 98.4%)

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-b89b1c03e8884d89b016753b6eee3e81
Source dataset
uspto-grants-2009_08
Patent number
US07576125B2

Reaction notes

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