Hydrochloric Acid → Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-

HRID 359916Notes

Reaction equation

HRID 359916 reaction equation
C[Si]([C:5]#[N:6])(C)C.[O:7]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl>C(Cl)(Cl)Cl.[Ti]>[C:5]([CH:17]([OH:18])[C:16]1[CH:19]=[CH:20][CH:21]=[C:14]([O:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:15]=1)#[N:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 382843-PhenoxybenzaldehydeHCID 82115Trimethylsilyl cyanide

Product 1

HCID 93218Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-Yield 64.4%

Reagents, catalysts & solvents 2

HCID 23963TitaniumCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of L-(+)-diisopropyl tartarate (1.030 mg, 4.4 mmol) in absolute chloroform (40 ml), tetaraisopropyl titanate (1.136 mg, 4 mmol) was dropwise added and stirred at room temperature for 30 minutes. After evaporating volatile components off in the same manner as in Example 1, absolute chloroform (40 ml) was added to the residue and stirred at room temperature to obtain a homogeneous solution. To the resulting solution, trimethylsilyl cyanide (436 mg, 4.4 mmol) and then 3-phenoxybenzaldehyde (793 mg, 4 mmol) were added and stirred at room temperature for 14 hours. Thereafter, 1N hydrochloric acid (40 ml) was added and stirred at room temperature for 30 minutes. Then, the reaction mixture was extracted with dichloromethane and dried over sodium sulfate followed by evaporation of the solvent to give an oily product. The product was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate) to obtain α-cyano-3-phenoxybenzyl alcohol (580 mg).

Workup

  1. customAfter evaporating volatile components off in the same manner as in Example 1, absolute chloroform (40 ml)
  2. additionwas added to the residue
  3. stirringstirred at room temperature
  4. customto obtain a homogeneous solution
  5. stirringstirred at room temperature for 14 hours
  6. stirringstirred at room temperature for 30 minutes
  7. extractionThen, the reaction mixture was extracted with dichloromethane
  8. dry with materialdried over sodium sulfate
  9. customfollowed by evaporation of the solvent
  10. customto give an oily product
  11. customThe product was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cbc4fa5366fa44d6925a45849303651b
Source dataset
uspto-grants-1991_03
Patent number
US05003083

Reaction notes

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