Water → 3-Oxo-2-(2,4,6-trimethyl-phenyl)-propionitrile

HRID 376490

Reaction equation

HRID 376490 reaction equation
C[O-].[Na+].[CH:4](OCC)=[O:5].[CH3:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[C:11]=1[CH2:18][C:19]#[N:20].O>C1C=CC=CC=1>[CH:4]([CH:18]([C:11]1[C:12]([CH3:17])=[CH:13][C:14]([CH3:16])=[CH:15][C:10]=1[CH3:9])[C:19]#[N:20])=[O:5]

Participants

6

Reactant 4

HCID 962WaterHCID 8025Ethyl formateHCID 5206982,4,6-TrimethylphenylacetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 224743973-Oxo-2-(2,4,6-trimethyl-phenyl)-propionitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred mixture of sodium methoxide (2.78 g, 51 mmol) and ethyl formate (4.0 g, 54 mmol) in 100 mL of benzene was added 2,4,6 trimethylphenylacetonitrile (8.0 g, 50 mmol) over 5 min. After stirring for an additional hour it was treated with water (100 mL) and the layers were separated. The aqueous layer was separated and acidified with 10% HCl and extracted with ethyl acetate. After drying the solvent was removed in vacuo to afford a-formyl-2,4,6-trimethylphenylacetonitrile as colorless crystals melting at 120-122° C.

Workup

  1. customthe layers were separated
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. customAfter drying the solvent
  5. customwas removed in vacuo

Sources & evidence

ORD record
ord-022ef2b446e247baaf1fb171f3f0df3e
Source dataset
uspto-grants-2000_02
Patent number
US06020492

Linked notes

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