2-Nitro-2-phenyl-1,3-propanediol → 2-Phenyl-1,3-propanediol

HRID 1460866Notes

Reaction equation

HRID 1460866 reaction equation
[N+]([C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH2:7][OH:8])[CH2:5][OH:6])([O-])=O.[H][H]>[Pd].CO>[C:9]1([CH:4]([CH2:5][OH:6])[CH2:7][OH:8])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 2243932-Nitro-2-phenyl-1,3-propanediolHCID 178418361HCID 178418361, compound

Product 1

HCID 2541782-Phenyl-1,3-propanediol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

12 g. (0.06 mole) of 2-nitro-2-phenyl-1,3-propanediol, 400 mg. of 5% palladium on calcium carbonate and 150 ml. of methanol are placed in a Parr hydrogenator bottle and reduced with hydrogen overnight. The mixture is filtered through Celite, concentrated to an oil and recrystallized from 30 ml. of toluene. The yield is 7.4 g. (80%) of product, M.P. 52°-4° C.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. concentrationconcentrated to an oil
  3. customrecrystallized from 30 ml

Sources & evidence

ORD record
ord-ae0c7467800240ea8e0b36f915f90841
Source dataset
uspto-grants-1991_12
Patent number
US05072056

Reaction notes

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