Benzaldehyde → HCID 9898969, compound

HRID 2249359Notes

Reaction equation

HRID 2249359 reaction equation
[C-]#N.[K+].[CH:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:12]1C(C)=CC=C[C:13]=1C.O.[CH3:21][C:22]([O:24]C(C)=O)=O>C(Cl)Cl>[C:22]([O:11][C@@H:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:13]#[N:12])(=[O:24])[CH3:21]

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 962WaterHCID 7918Acetic AnhydrideHCID 79372,6-LutidineHCID 9032Potassium Cyanide

Product 1

HCID 9898969HCID 9898969, compoundYield 642.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a mixture of KCN (5.0 g, 77 mmol) and catalyst 1a (R1=R2=tBu)(0.3 g, 0.25 mmol) in CH2Cl2 (60 ml) were added with stirring benzaldehyde (2.5 ml, 25 mmol), 2,6-lutidine (0.28 ml, 2.4 mmol) and water (0.4 ml, 24 mmol). The reaction mixture was cooled to −30° C. and Ac2O (5 ml, 53 mmol) was added. The reaction mixture was stirred for 10 hours at −30° C. and then filtered, passed through a SiO2 column (1 cm×10 cm) in a mixture of hexane/AcOEt 10:1 to remove the catalyst. The filtrate was evaporated and distilled in vacuo to give 2.7 g (63%) of O-Acetyl (S)-mandelonitrile with 87% enantiomeric excess as determined by chiral gas chromatography.

Workup

  1. filtrationfiltered
  2. additionpassed through a SiO2 column (1 cm×10 cm) in a mixture of hexane/AcOEt 10:1
  3. customto remove the catalyst
  4. customThe filtrate was evaporated
  5. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-a3260f83a17241c8a9fb06d64a98efd4
Source dataset
uspto-grants-2008_01
Patent number
US07314844B2

Reaction notes

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