Phenylacetonitrile → trans-3-(beta-Cyanostyryl)-2,2-dimethyl-cyclopropanecarboxylic acid

HRID 443983

反応式

HRID 443983 の反応式
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O-]CC.[Na+].C([O:16][C:17]([CH:19]1[CH:21]([CH:22]=O)[C:20]1([CH3:25])[CH3:24])=[O:18])C>C(O)C>[C:8]([C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[CH:22][C@H:21]1[C@H:19]([C:17]([OH:18])=[O:16])[C:20]1([CH3:25])[CH3:24])#[N:9]

参加物

5

反応物 3

HCID 8794PhenylacetonitrileHCID 566079Ethyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylateHCID 2723922Sodium ethoxide

生成物 1

HCID 86737697trans-3-(beta-Cyanostyryl)-2,2-dimethyl-cyclopropanecarboxylic acid

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

Phenylacetonitrile is added to a stirred solution of sodium ethoxide in absolute ethanol (prepared from 1.1 g sodium and 100 ml of ethanol). Next, a solution of 3-formyl-2,2-dimethyl-cyclopropanecarboxylic acid ethyl ester (8.5 g) in absolute ethanol (15 ml) is added over 5 minutes. The reaction mixture is stirred for 12 hours at room temperature and then heated on a steam bath for 0.5 hour. The alcohol is removed in vacuo, and the residue washed with water (250 ml) and ether (150 ml). The aqueous layer is acidified with concentrated hydrochloric acid. The resulting cream colored slurry is filtered and the isolated product dried. The product is dissolved in ether and precipitated with hexane to afford 6.1 g of white crystals, m.p. 186°-188° C.

後処理

  1. temperatureheated on a steam bath for 0.5 hour
  2. customThe alcohol is removed in vacuo
  3. washthe residue washed with water (250 ml) and ether (150 ml)
  4. filtrationis filtered
  5. customthe isolated product dried
  6. dissolutionThe product is dissolved in ether
  7. customprecipitated with hexane

出典と根拠

ORDレコード
ord-1e4f110c222d42fdb55abe6645faa667
出典データセット
uspto-grants-1981_04
特許番号
US04262117

関連ノート

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