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

HRID 443983

반응식

HRID 443983 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1e4f110c222d42fdb55abe6645faa667
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04262117

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