Acetone Cyanohydrin → (3S)-3-hydroxy-3-phenylpropanenitrile

HRID 846341Notes

Reaction equation

HRID 846341 reaction equation
[CH2:1]1[O:9][C@@H:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC(C)(O)[C:12]#[N:13].C(N(CC)CC)C>O1CCCC1>[C:3]1([C@@H:2]([OH:9])[CH2:1][C:12]#[N:13])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6406Acetone CyanohydrinHCID 8471TriethylamineHCID 114705(+)-Styrene oxide

Product 1

HCID 11084031(3S)-3-hydroxy-3-phenylpropanenitrileYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 40.0 g of (R)-styrene oxide, 31.12 g of acetone cyanohydrin, 36.96 g of triethylamine, and 150 ml of tetrahydrofuran was heated at reflux for 18 hours. The reaction mixture was cooled, concentrated in vacuo, diluted with 200 ml of 2N potassium hydroxide, and extracted with diethyl ether. The ether extracts were combined, dried over magnesium sulfate, and concentrated in vacuo providing 34.3 g of the title intermediate.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. additiondiluted with 200 ml of 2N potassium hydroxide
  6. extractionextracted with diethyl ether
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-031d64a9ec0c47989fe335f90f58eb3c
Source dataset
uspto-grants-1992_08
Patent number
US05136078

Reaction notes

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