Sulfuric Acid → Methyl (3R)-4-cyano-3-hydroxybutanoate

HRID 1356575Notes

Reaction equation

HRID 1356575 reaction equation
[C:1]([CH2:3][C@@H:4]([OH:9])[CH2:5][C:6]([OH:8])=[O:7])#[N:2].S(=O)(=O)(O)O.[C:15](=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:15][O:7][C:6](=[O:8])[CH2:5][C@H:4]([OH:9])[CH2:3][C:1]#[N:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 10236005(R)-4-cyano-3-hydroxybutyric acid

Product 1

HCID 10149003Methyl (3R)-4-cyano-3-hydroxybutanoateYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-4-cyano-3-hydroxybutyric acid (1.0 mol) in methanol (500 ml) and conc. sulfuric acid (5 g) were refluxed for 5 hours. The reaction mixture was neutralized with sodium carbonate and filtered. The filtrate was concentrated in vacuo to afford (R)-4-cyano-3-hydroxybutyric acid methyl ester (130 g, 91%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-88710c1f836f49869471671e60213968
Source dataset
uspto-grants-2003_07
Patent number
US06586616B1

Reaction notes

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