Benzaldehyde → Mandelonitrile

HRID 868508Notes

Reaction equation

HRID 868508 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:9]#[N:10].[K+].S(=O)(=O)(O)O>O>[CH:5]1[CH:6]=[CH:7][C:2]([CH:1]([OH:8])[C:9]#[N:10])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 1118Sulfuric AcidHCID 9032Potassium Cyanide

Product 1

HCID 10758Mandelonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 ml four-neck round bottom flask was equipped with a magnetic stirring bar, water condenser, addition funnel and drying tube. The glassware was dried and to this was charged 21.2 grams (0.2 mole) benzaldehyde and 19.5 grams (0.3 mole) potassium cyanide dissolved in 70 ml of water. The reaction flask was cooled to 10°-15° C. using a water/ice bath. To this was added 70 ml of 40% sulfuric acid over a 60 minute period. After the addition was complete, the reaction was allowed to warm to room temperature and stir for an additional two hours. At the end of this time the reaction mixture was extracted with carbon tetrachloride (3×75 ml), washed the combined carbon tetrachloride layers with water (2×50 ml), dried the carbon tetrachloride layer with anhydrous magnesium sulfate, filtered and concentrated to yield benzaldehyde cyanohydrin.

Workup

  1. customA 500 ml four-neck round bottom flask was equipped with a magnetic stirring bar, water condenser, addition funnel
  2. customdrying tube
  3. customThe glassware was dried
  4. temperatureThe reaction flask was cooled to 10°-15° C.
  5. additionAfter the addition
  6. extractionAt the end of this time the reaction mixture was extracted with carbon tetrachloride (3×75 ml)
  7. washwashed the combined carbon tetrachloride layers with water (2×50 ml)
  8. dry with materialdried the carbon tetrachloride layer with anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-64c421b95df24080ad1ec947637b0132
Source dataset
uspto-grants-1988_10
Patent number
US04780458

Reaction notes

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