3-Cyanobenzoic acid → Benzoic acid, 3-cyano-, methyl ester

HRID 1873587Notes

Reaction equation

HRID 1873587 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])#[N:2].[CH3:12][Si](C=[N+]=[N-])(C)C>C1(C)C=CC=CC=1.CO.CCCCCC>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([O:8][CH3:12])=[O:7])#[N:2]

Participants

6

Reactant 2

HCID 158753-Cyanobenzoic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 83554Benzoic acid, 3-cyano-, methyl ester

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

100 mg (0.68 mmol) of 3-cyanobenzoic acid are initially charged in 4 ml of toluene and 3.5 ml of methanol, and 0.51 ml (1.02 mnmol) of a 2 M solution of trimethylsilyldiazomethane in n-hexane is added at RT. The reaction mixture is stirred at RT for 1.5 h. After removal of the solvent on a rotary evaporator the residue is dried under reduced pressure. The product is obtained in pure form and is directly reacted further.

Workup

  1. customAfter removal of the solvent
  2. customon a rotary evaporator the residue
  3. customis dried under reduced pressure
  4. customThe product is obtained in pure form
  5. customis directly reacted further

Sources & evidence

ORD record
ord-987ee710b4694e0cb1bb0da5a2c90820
Source dataset
uspto-grants-2012_11
Patent number
US08304412B2

Reaction notes

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