Formic Acid → 4'-Methyl[1,1'-biphenyl]-2-carbaldehyde

HRID 2427896Notes

Reaction equation

HRID 2427896 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)#N.C(O)=[O:17]>[Ni]>[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=[O:17]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 1455122-Cyano-4'-methylbiphenyl

Product 1

HCID 13940094'-Methyl[1,1'-biphenyl]-2-carbaldehydeYield 71.2%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
85 °C

Procedure

To a solution of 10 g (0.051 mol) of 4-(2-cyanophenyl)toluene in 300 ml of formic acid 30 g of Raney Ni is added. Reaction mixture is stirred at the 85° C. overnight and filtered. Filter cake is washed with 50 ml of dichloromethane. 150 ml of water are added to the filtrate, mixture is stirred for 10 minutes and layers separated. Organic layer is dried over MgSO4 and evaporated under reduced pressure giving 7.13 g of oily residue, which is purified on chromatographic column (silica gel, petroleum ether:ether 4:1) to produce 5.23 g of pure product in a form of a brown oil.

Workup

  1. customReaction mixture
  2. filtrationfiltered
  3. filtrationFilter cake
  4. washis washed with 50 ml of dichloromethane
  5. addition150 ml of water are added to the filtrate, mixture
  6. stirringis stirred for 10 minutes
  7. customlayers separated
  8. dry with materialOrganic layer is dried over MgSO4
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-60c748ed953147d5a21e5fe56492000a
Source dataset
uspto-grants-2011_06
Patent number
US07968727B2

Reaction notes

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