Benzyl Alcohol → HCID 69940102, compound

HRID 1356579Notes

Reaction equation

HRID 1356579 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9]([CH2:11][C@@H:12]([OH:17])[CH2:13][C:14](O)=[O:15])#[N:10].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.S(=O)(=O)(O)O>[CH2:1]([O:8][C:14](=[O:15])[CH2:13][C@H:12]([OH:17])[CH2:11][C:9]#[N:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 10340Sodium CarbonateHCID 10236005(R)-4-cyano-3-hydroxybutyric acid

Product 1

HCID 69940102HCID 69940102, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6342AcetonitrileSolvent

Procedure

Benzylalcohol (216 g, 2 eq.) and conc. sulfuric acid (5 g) were added to (R)-4-cyano-3-hydroxybutyric acid (1.0 mol) dissolved in acetonitrile (500 ml) and 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 benzyl ester (157 g, 92%) which was purified by column chromatography on a silica gel.

Workup

  1. temperaturerefluxed for 5 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a95b9850548541d9ae65b1bb98f31c62
Source dataset
uspto-grants-2003_07
Patent number
US06586616B1

Reaction notes

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