Benzyl Alcohol → 1-Phenyl-1,2-ethanediol

HRID 1048915Notes

Reaction equation

HRID 1048915 reaction equation
[CH2:1]([OH:3])C.C([O-])=O.[NH4+].C(O)=O.[CH2:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Pd].O>[C:12]1([CH:11]([OH:18])[CH2:1][OH:3])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 284Formic AcidHCID 702EthanolHCID 2723923Ammonium formate

Product 1

HCID 71491-Phenyl-1,2-ethanediolYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Pd/C (5 mol %) is weighed into a reaction flask. A solvent mixture consisting of ethanol and water (4:1) and ammonium formate (30 mol %) is added, the reaction flask is capped with a rubber septa and the mixture is heated (80° C.) for 2 minutes. Formic acid (3 equivalents) and then benzyl alcohol are added by syringe. The reaction is run for 10-40 minutes and the reaction is quenched with brine. The product is extracted by DCM and the organic phase is dried by Na2SO4. The product 1-phenyl-2-propanol was analyzed by 1H NMR and produced in 60% yield.

Workup

  1. additionis added
  2. customthe reaction flask is capped with a rubber septa
  3. customthe reaction is quenched with brine
  4. extractionThe product is extracted by DCM
  5. dry with materialthe organic phase is dried by Na2SO4
  6. customproduced in 60% yield

Sources & evidence

ORD record
ord-b4ac2a14e8dc4693ac1ae5b327c32a8c
Source dataset
uspto-grants-2016_07
Patent number
US09382225B2

Reaction notes

Loading…