Hydrochloric Acid → 4-Formyl-3-hydroxy-2-methylbenzonitrile

HRID 629369Notes

Reaction equation

HRID 629369 reaction equation
[OH:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[Cl-].[Mg+2].[Cl-].[CH2:14]=[O:15].Cl>C1COCC1.C(N(CC)CC)C>[CH:14]([C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([CH3:10])[C:2]=1[OH:1])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5360315Magnesium ChlorideHCID 226160943-Hydroxy-2-methylbenzonitrile

Product 1

HCID 1184682924-Formyl-3-hydroxy-2-methylbenzonitrileYield 15.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 3-hydroxy-2-methylbenzonitrile (7.00 g) in THF (100 mL) were added triethylamine (13.1 g), magnesium chloride (12.4 g) and paraformaldehyde (6.60 g), and the mixture was heated with reflux for 16 hr under nitrogen atmosphere. The reaction mixture was poured into 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (1.30 g).

Workup

  1. temperaturethe mixture was heated
  2. temperaturewith reflux for 16 hr under nitrogen atmosphere
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash silica gel column chromatography (ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-0eca85aa837d46939ac19b533649bf5c
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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