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

HRID 322005ノート

反応式

HRID 322005 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 701428183-Hydroxy-2-(2,4,6-trimethylphenyl)acrylonitrile収率 52.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c794c31b48bc445db7775a3dd6d62cd5
出典データセット
uspto-grants-2001_04
特許番号
US06211195B1

反応ノート

読み込み中…