Potassium Cyanide → Methyl 4-cyano-2-(2-methylphenyl)benzoate

HRID 2121259Notes

Reaction equation

HRID 2121259 reaction equation
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH:3]=1.[C-:19]#[N:20].[K+]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:19]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])[CH:3]=1)#[N:20]

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 11508596HCID 11508596, compound

Product 1

HCID 11615778Methyl 4-cyano-2-(2-methylphenyl)benzoateYield 88.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The compound from Example 954B (1.55 g, 4.41 mmol) was dissolved in 10 mL of THF. Then Pd(PPh3)4 (120 mg, 2.2% eq) and powdered KCN (430 mg, 6.61 mmol, 1.5 eq) was added. The mixture was refluxed for 12 hr. GC/MS showed all the starting material was converted to the product. The mixture was extracted with ethyl acetate and water. After evaporation of solvents, the residue was purified by flash column chromatography (10:1=hexane/ethyl acetate) to give an oily product (978 mg, 88% yield). 1H NMR (CDCl3) δ 8.02 (d, J=8.1 Hz, 1H), 7.72 (d, J=7.9 Hz, 1H), 7.56 (s, 1H), 7.20-7.33 (m, 3H), 7.03 (d, J=7.4 Hz, 1H), 3.63 (s, 3H), 2.06 (s, 3H); 13C NMR (CDCl3) δ 165.9, 143.0, 138.5, 134.6, 134.2, 133.9, 130.3, 130.0, 129.3, 127.9, 127.6, 125.0, 117.3, 114.6, 51.8, 19.4.

Workup

  1. temperatureThe mixture was refluxed for 12 hr
  2. extractionThe mixture was extracted with ethyl acetate and water
  3. customAfter evaporation of solvents
  4. customthe residue was purified by flash column chromatography (10:1=hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c72d514ec09c4d0385597aa256fc7991
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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