Ethyl Acetate → Methyl 5-cyano-2-methoxy-4-(1-methylethyl)benzoate

HRID 1883577Notes

Reaction equation

HRID 1883577 reaction equation
[Cu][C:2]#[N:3].[CH3:4][O:5][C:6]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[C:13](Br)=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9].C(OCC)(=O)C>CN1CCCC1=O>[CH3:4][O:5][C:6]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[C:13]([C:2]#[N:3])=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21956813HCID 21956813, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 21956833Methyl 5-cyano-2-methoxy-4-(1-methylethyl)benzoateYield 74.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Copper (I) cyanide (550 mg, 6 mmol) was added to a solution of methyl 2-methoxy-5-bromo-4-iso-propylbenzoate (861 mg) in N-methyl-2-pyrolidinone (30 ml). The mixture was stirred under argon and boiled under reflux for 4 h. The mixture was cooled, poured into excess ice/water and ethyl acetate and filtered. The organic phase was separated, washed with water, brine and dried(MgSO4). Evaporation gave a crude brown solid which was purified by chromatography on silica gel eluting with ethyl acetate/n-hexane (1:4). The product was obtained as a white solid (523 mg).

Workup

  1. temperatureunder reflux for 4 h
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customThe organic phase was separated
  5. washwashed with water, brine and dried(MgSO4)
  6. customEvaporation
  7. customgave a crude brown solid which
  8. customwas purified by chromatography on silica gel eluting with ethyl acetate/n-hexane (1:4)

Sources & evidence

ORD record
ord-11383f619478402b80a97889fe34d9d3
Source dataset
uspto-grants-2004_07
Patent number
US06762192B2

Reaction notes

Loading…