Benzyl Alcohol → (1-Methoxyethyl)benzene

HRID 1048916Notes

Reaction equation

HRID 1048916 reaction equation
[CH2:1]([OH:3])[CH3:2].C([O-])=O.[NH4+].[CH:8](O)=O.C(O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>[Pd].O>[CH3:8][O:3][CH:1]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2]

Participants

7

Reactant 4

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

Product 1

HCID 19913(1-Methoxyethyl)benzeneYield 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 20 minutes and the reaction is quenched with brine. The product is extracted by DCM and the organic phase is dried by Na2SO4. The product ethylbenzene 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-3839bc70275546d4bb6735f4662b7e8f
Source dataset
uspto-grants-2016_07
Patent number
US09382225B2

Reaction notes

Loading…