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

HRID 1374273Notes

Reaction equation

HRID 1374273 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].[C:12](Cl)(=O)C(Cl)=O>ClCCl.CN(C=O)C>[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

5

Reactant 2

HCID 158753-Cyanobenzoic acidHCID 65578Oxalyl chloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Preparation H11, Step 1: 10 g (0.068 mol) of 3-cyano benzoic acid was taken in 150 ml of dry dichloromethane and cooled to 0° C. Added 50 ml of oxalyl chloride drop wise followed by 5 drops of dry DMF. The reaction mixture was stirred at RT overnight. Dichloromethane was removed and dry methanol (50 ml) was added and stirred at rt for 2 h. Excess methanol was removed and the residue was dissolved in ethyl acetate. The ethyl acetate layer was washed with 10% of sodium bicarbonate, brine and concentrated to give methyl 3-cyanobenzoate (7 g) as a white solid.

Workup

  1. customPreparation H11, Step 1
  2. customDichloromethane was removed
  3. additiondry methanol (50 ml) was added
  4. stirringstirred at rt for 2 h
  5. customExcess methanol was removed
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washThe ethyl acetate layer was washed with 10% of sodium bicarbonate, brine
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bd754139c4a742c08af7a99dd3bfe6dd
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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