Sodium Hydroxide → 3-Methoxy-2-methylbenzonitrile

HRID 1107715Notes

Reaction equation

HRID 1107715 reaction equation
Cl.[NH2:2]O.[CH3:4][O:5][C:6]1[C:7]([CH3:14])=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=O.[OH-].[Na+]>C(O)=O>[CH3:4][O:5][C:6]1[C:7]([CH3:14])=[C:8]([CH:11]=[CH:12][CH:13]=1)[C:9]#[N:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 131626633-Methoxy-2-methylbenzaldehyde

Product 1

HCID 110947703-Methoxy-2-methylbenzonitrileYield 80%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Hydroxylamine hydrochloride (0.75 g, 11 mmol) was added to 3-methoxy-2-methylbenzaldehyde (1.25 g, 8.32 mmol) in formic acid (89-91%) (10 ml), and the mixture heated to reflux for 40 min., cooled, diluted with ice-cold water, basified with 10% aqueous sodium hydroxide solution and extracted with diethyl ether. The organic extract was washed with saturated aqueous sodium chloride (50 ml), dried over magnesium sulphate and evaporated. The residue was purified by flash chromatography over silica gel eluting with 5% diethyl ether in hexane to afford the product as a white solid (0.98 g). M+ 147; 360 MHz 1H n.m.r (CDCl3) 7.26-7.17 (2H, m), 7.02 (1H, d, J 7.9 Hz), 3.86 (3H, s), 2.41 (3H, s).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 40 min.
  3. temperaturecooled
  4. additiondiluted with ice-cold water
  5. extractionextracted with diethyl ether
  6. extractionThe organic extract
  7. washwas washed with saturated aqueous sodium chloride (50 ml)
  8. dry with materialdried over magnesium sulphate
  9. customevaporated
  10. customThe residue was purified by flash chromatography over silica gel eluting with 5% diethyl ether in hexane

Sources & evidence

ORD record
ord-9f70d035c6c641d08f2557ab721148a2
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

Loading…