Water → 3-Hydroxy-2-(2,4,6-trimethylphenyl)acrylonitrile

HRID 1383303

Reaction equation

HRID 1383303 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[CH2:10][C:11]#[N:12].[CH:13](OCC)=[O:14].[O-]CC.[Na+].O>C(O)C>[OH:14][CH:13]=[C:10]([C:3]1[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[CH3:1])[C:11]#[N:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8025Ethyl formateHCID 5206982,4,6-TrimethylphenylacetonitrileHCID 2723922Sodium ethoxide

Product 1

HCID 701428183-Hydroxy-2-(2,4,6-trimethylphenyl)acrylonitrileYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 2,4,6-trimethylphenylacetonitrile (75 g) and ethyl formate (67 g) in 225 ml absolute ethanol was treated with solid sodium ethoxide (36 g) in small portions over 10 minutes, with good stirring. The mixture was heated to 60° C. under nitrogen for 16 hours and allowed to cool to room temperature. The reaction mixture was poured into 1.2 liters of water, extracted with diethyl ether (3×200 ml). The aqueous phase was acidified with 6M HCl to pH=1 and extracted with ethyl acetate. The ethyl acetate extract was washed with brine, dried over MgSO4 and concentrated, yielding 46 g (98%) of 3-hydroxy-2-(2,4,6-trimethylphenyl)acrylonitrile (intermediate 1).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with diethyl ether (3×200 ml)
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. washwas washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-982bb3752ab5436fbe57d48d351bda6f
Source dataset
uspto-grants-2001_07
Patent number
US06255310B1

Linked notes

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