2-Cyano-3-(4-methoxyphenyl)prop-2-enoic acid → 2-Cyano-3-(4-methoxyphenyl)propanoic acid

HRID 280158Notes

Reaction equation

HRID 280158 reaction equation
[BH4-].[Na+].[C:3]([C:5](=[CH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7])#[N:4]>C([O-])(O)=O.[Na+].CO>[C:3]([CH:5]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH3:17])=[CH:14][CH:15]=1)[C:6]([OH:8])=[O:7])#[N:4]

Participants

5

Reactant 2

HCID 2332602-Cyano-3-(4-methoxyphenyl)prop-2-enoic acidHCID 4311764Sodium borohydride

Product 1

HCID 137111482-Cyano-3-(4-methoxyphenyl)propanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
15 °C

Procedure

Sodium borohydride (30.2 g) is added portionwise over a period of 2 hours to a stirred mixture of α-cyano-4-methoxycinnamic acid (52.5 g) in aqueous saturated NaHCO3 (200 ml) and methanol (600 ml) cooled to about 15° C. The reaction mixture is allowed to warm to RT, stirred at RT for 30 min and concentrated in vacuo. The residue is partitioned between water and ether and the aqueous layer acidified and extracted with ether. The ether extract is washed, dried over Na2SO4, filtered and the filtrate evaporated in vacuo producing a liquid which is crystallized from toluene yielding the desired product as a solid, M.P. 94°-95° C.

Workup

  1. temperatureto warm to RT
  2. concentrationconcentrated in vacuo
  3. customThe residue is partitioned between water and ether
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. washis washed
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe filtrate evaporated in vacuo
  10. customproducing a liquid which
  11. customis crystallized from toluene yielding the desired product as a solid, M.P. 94°-95° C.

Sources & evidence

ORD record
ord-7972baea32cc4cc7931ce23c3aafa90e
Source dataset
uspto-grants-1986_05
Patent number
US04588719

Reaction notes

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