Potassium Cyanide → Ethyl 4-cyano-3,5-dimethylbenzoate

HRID 1282061Notes

Reaction equation

HRID 1282061 reaction equation
N[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[CH3:14].S([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[Cu](C#N)[C:28]#[N:29].[C-]#N.[K+]>Cl.O.C(OCC)(=O)C>[C:28]([C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[CH3:14])#[N:29]

Participants

9

Reactant 5

HCID 9032Potassium CyanideHCID 10340Sodium CarbonateHCID 24437Sodium SulfiteHCID 201013Benzoic acid, 4-amino-3,5-dimethyl-, ethyl esterHCID 178418260HCID 178418260, compound

Product 1

HCID 18423069Ethyl 4-cyano-3,5-dimethylbenzoateYield 79.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 4-aminomesitylenate (6.6 g) in conc. hydrochloric acid (50 ml) was added a solution of sodium sulfite (2.6 g) in water (15 ml) at 0-5° C. over 30 min. This reaction mixture was stirred at 0° C. for 1 hr. To this reaction mixture was neutralized by adding sodium carbonate and then ethyl acetate (100 ml) was added. To a solution of copper cyanide (6.8 g) in water (100 ml) was added potassium cyanide (18 g) and the mixture was stirred at 0° C. for 30 min. The above-mentioned reaction mixture was added at 0-5° C. and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was extracted with ethyl acetate, washed with aqueous sodium hydrogencarbonate and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the obtained residue was recrystallized from ethyl acetate-hexane to give the title compound (5.5 g) as pale-brown crystals.

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 min
  2. additionThe above-mentioned reaction mixture was added at 0-5° C.
  3. stirringthe mixture was stirred at 0° C. for 1 hr
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washwashed with aqueous sodium hydrogencarbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe obtained residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-7da742c58c844bc5aa99fdee28231449
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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