Sodium borohydride → 2-Cyano 3-(2,6-dichlorophenyl)propanoic acid

HRID 1026622Notes

Reaction equation

HRID 1026622 reaction equation
[BH4-].[Na+].[C:3]([C:5](=[CH:9][C:10]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:17])[C:6]([OH:8])=[O:7])#[N:4]>CO.C(=O)(O)[O-].[Na+]>[C:3]([CH:5]([CH2:9][C:10]1[C:11]([Cl:17])=[CH:12][CH:13]=[CH:14][C:15]=1[Cl:16])[C:6]([OH:8])=[O:7])#[N:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 545137902-Cyano-3-(2,6-dichlorophenyl)acrylic acid

Product 1

HCID 135607172-Cyano 3-(2,6-dichlorophenyl)propanoic acidYield 100.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (1121 mmol, 42.4 g) was added, in portions over a period of 45 minutes, to a stirred suspension of 2-cyano-3-(2,6-dichlorophenyl)acrylic acid (448 mmol, 108.5 g) in MeOH (1 L) and aqueous saturated sodium bicarbonate (500 mL) at 0° C. After stirring at 0° C. for 30 minutes the cooling bath was removed and the reaction was allowed to warm to room temperature. Stirring was continued at room temperature for 3 hours and the reaction mixture was then left to stand overnight. The reaction mixture was partially concentrated under reduced pressure and the remaining aqueous was diluted with water and then acidified with 5 N HCl. Extraction with ether followed by drying over sodium sulfate, filtering and concentrating under reduced pressure afforded 110 g of 2-cyano-3-(2,6-dichlorophenyl)propanoic acid (100% yield).

Workup

  1. customwas removed
  2. temperatureto warm to room temperature
  3. stirringStirring
  4. waitwas continued at room temperature for 3 hours
  5. waitthe reaction mixture was then left
  6. waitto stand overnight
  7. concentrationThe reaction mixture was partially concentrated under reduced pressure
  8. additionthe remaining aqueous was diluted with water
  9. extractionExtraction with ether
  10. dry with materialby drying over sodium sulfate
  11. filtrationfiltering
  12. concentrationconcentrating under reduced pressure

Sources & evidence

ORD record
ord-0dd3e07cd54d4a8881c264bf6c45c76e
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

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