Water → O-(p-toluenesulfonyl)-m-benzoylmandelonitrile

HRID 1759423Notes

Reaction equation

HRID 1759423 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1.[C-:28]#[N:29].[Na+].O>COCCOC>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:13][CH:12]([C:11]2[CH:14]=[CH:15][CH:16]=[C:9]([C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:10]=2)[C:28]#[N:29])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 8929Sodium CyanideHCID 130201683-Benzoylbenzaldehyde

Product 1

HCID 12945137O-(p-toluenesulfonyl)-m-benzoylmandelonitrileYield 67%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

m-Benzoylbenzaldehyde (4.20 g) and 3.80 g of p-toluenesulfonyl chloride were dissolved in 13 ml of 1,2-dimethoxyethane (DME), and the solution was stirred at -15° to -10° C. An aqueous solution of sodium cyanide (1.08 g/15 ml) was added dropwise to the solution over 10 minutes. The mixture was stirred at -15° to -10° C. for 2 hours and then at room temperature for 40 minutes. Water (60 ml) was added, and the mixture was extracted with 60 ml of methylene chloride three times. The extract was washed with 70 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was separated by column chromatography (silica gel; benzene and methylene chloride) to afford 5.21 g (yield 67%) of O-(p-toluenesulfonyl)-m-benzoylmandelonitrile as colorless crystals.

Workup

  1. stirringThe mixture was stirred at -15° to -10° C. for 2 hours
  2. extractionthe mixture was extracted with 60 ml of methylene chloride three times
  3. washThe extract was washed with 70 ml of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated by column chromatography (silica gel; benzene and methylene chloride)

Sources & evidence

ORD record
ord-aa94136bfa5046d19223b2eddb8c72f7
Source dataset
uspto-grants-1982_07
Patent number
US04340740

Reaction notes

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