Benzaldehyde → Mandelonitrile, (+)-

HRID 359913Notes

Reaction equation

HRID 359913 reaction equation
C(O)(=O)[C@@H]([C@H](C(O)=O)O)O.C[Si]([C:15]#[N:16])(C)C.[CH:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:15]([C@H:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)#[N:16]

Participants

4

Procedure

To a solution of L(+)-tartaric acid derivative shown in Table 1 (2 mmol) in a solvent shown in Table 1 (20 ml), a tetraalkyl titanate shown in Table 1 (2 mmol) was dropwise added and stirred for 30 minutes at room temperature. After evaporating volatile components off in the same manner as in Example 1, a solvent shown in Table 1 (20 ml) was added to the residue and stirred at room temperature to obtain a homogeneous solution. To the resulting solution, trimethylsilylcyanide (218 mg) and then benzaldehyde (212 mg) were added and stirred for 14 hours at room temperature. After the reaction, the reaction mixture was treated in the same manner as in Example 1. The product was analyzed by HPLC. The results are shown in Table 1.

Workup

  1. additionwas dropwise added
  2. customAfter evaporating volatile components off in the same manner as in Example 1
  3. additionwas added to the residue
  4. stirringstirred at room temperature
  5. customto obtain a homogeneous solution
  6. stirringstirred for 14 hours at room temperature
  7. customAfter the reaction
  8. additionthe reaction mixture was treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-4a4c91b670034a519e3a0e0daaf5f25c
Source dataset
uspto-grants-1991_03
Patent number
US05003083

Reaction notes

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