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

HRID 322005Notes

Reaction equation

HRID 322005 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 52.2%

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, was allowed to cool to room temperature, and then poured into 1.2 l of water. This mixture was extracted with ether. The aqueous phase was acidified with 6M HCl to pH 1 and extracted with ethyl acetate. The ethyl acetate extracts were combined, washed with water and brine, dried and concentrated to give 46 g of 3-hydroxy-2-(2′,4′,6′-trimethylphenyl)acrylonitrile (intermediate 2). A sample was crystallized from ether/hexane to give colorless crystals, melting point=124-126° C.

Workup

  1. temperatureto cool to room temperature
  2. extractionThis mixture was extracted with ether
  3. extractionextracted with ethyl acetate
  4. washwashed with water and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c794c31b48bc445db7775a3dd6d62cd5
Source dataset
uspto-grants-2001_04
Patent number
US06211195B1

Reaction notes

Loading…