Water → Ethyl 2-formylbiphenyl-4-carboxylate

HRID 731929Notes

Reaction equation

HRID 731929 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C[N+]1([O-])CC[O:24]CC1.O>C(#N)C>[CH:2]([C:3]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:24]

Participants

5

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 23112214Ethyl 2-(bromomethyl)biphenyl-4-carboxylate

Product 1

HCID 23112255Ethyl 2-formylbiphenyl-4-carboxylateYield 66.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In 100 ml of acetonitrile was dissolved 9.3 g of ethyl 2-(bromomethyl)biphenyl-4-carboxylate, and 7.0 g of N-methylmorpholine-N-oxide was added thereto at room temperature, followed by 4 hours of stirring. Water was added to the reaction solution, which was then extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate. After the solvent was removed by evaporation, the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to obtain 4.94 g of ethyl 2-formylbiphenyl-4-carboxylate as a white solid.

Workup

  1. additionwas added
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  4. customAfter the solvent was removed by evaporation
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-98154ab59f1f4f2585d1fb8f3e60d177
Source dataset
uspto-grants-2009_09
Patent number
US07585878B2

Reaction notes

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