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

HRID 2285950Notes

Reaction equation

HRID 2285950 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-07f47bd3d32147b885c99606cafccabc
Source dataset
uspto-grants-1982_04
Patent number
US04325969

Reaction notes

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