Diisopropyl Ether → Benzeneacetonitrile, alpha-hydroxy-3-phenoxy-, (alphaS)-

HRID 1395125Notes

Reaction equation

HRID 1395125 reaction equation
S(=O)(O)[O-].[O:5]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=[O:16])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C-:20]#[N:21].[Na+].C(OC(C)C)(C)C>C(O)(=O)C.O.CN(C)C=O>[C:20]([CH:15]([OH:16])[C:14]1[CH:17]=[CH:18][CH:19]=[C:12]([O:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:13]=1)#[N:21]

Participants

8

Reactant 4

HCID 7914Diisopropyl EtherHCID 8929Sodium CyanideHCID 382843-PhenoxybenzaldehydeHCID 104748Bisulfite

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

20 g of anhydrous combination bisulfite of m-phenoxy-benzaldehyde were added under an inert atmosphere to 80 ml of anhydrous dimethylformamide and then 3.3 g of anhydrous sodium cyanide were added thereto at 0° C. under an inert atmosphere. The mixture was stirred at 0° C. for 45 minutes after which a sample of the reaction mixture was taken to verify by chromatography analysis that the conversion was complete. The reaction mixture was poured into a mixture of ice, water, acetic acid and isopropyl ether and the mixture was stirred and decanted. The aqueous phase was extracted with isopropyl ether and the combined organic phases were washed with water, dried and evaporated to dryness to obtain 13.8 g of α-cyano-3-phenoxy-benzyl alcohol.

Workup

  1. customat 0° C.
  2. stirringthe mixture was stirred
  3. customdecanted
  4. extractionThe aqueous phase was extracted with isopropyl ether
  5. washthe combined organic phases were washed with water
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-057481a423f24e0fa4597b6460307c8d
Source dataset
uspto-grants-1980_05
Patent number
US04202835

Reaction notes

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