Ethanol → 3-(3'-Cyano-2'-hydroxypropyl)-benzhydrol

HRID 1579773Notes

Reaction equation

HRID 1579773 reaction equation
Cl[CH2:2][CH:3]([OH:19])[CH2:4][C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][CH:18]=1)[CH:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)C.[C-:23]#[N:24].[K+]>O>[C:23]([CH2:2][CH:3]([OH:19])[CH2:4][C:5]1[CH:6]=[C:7]([CH:16]=[CH:17][CH:18]=1)[CH:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[N:24]

Participants

5

Reactant 3

HCID 702EthanolHCID 9032Potassium CyanideHCID 214956193-(3'-Chloro-2'-hydroxypropyl)-benzhydrol

Product 1

HCID 214956743-(3'-Cyano-2'-hydroxypropyl)-benzhydrolYield 71.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 11.97 g of 3-(3'-chloro-2'-hydroxypropyl)-benzhydrol, 120 ml of ethanol, 2.4 ml of water and 2.66 g of potassium cyanide was refluxed for 3 hours and then evaporated to dryness. The residue was taken up in 200 ml of methylene chloride and the organic phase was washed with water, dried over sodium sulfate, treated with activated carbon, filtered and evaporated to dryness. The residue was chromatographed over silica and was eluted with a 75-25 methylene chloride-ethyl acetate mixture which was evaporated to obtain 7.8 g of 3-(3'-cyano-2'-hydroxypropyl)-benzhydrol in the form of an orange amorphous solid soluble in chloroform and insoluble in water.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customevaporated to dryness
  3. washthe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. additiontreated with activated carbon
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was chromatographed over silica
  9. washwas eluted with a 75-25 methylene chloride-ethyl acetate mixture which
  10. customwas evaporated

Sources & evidence

ORD record
ord-9f295fa57f7e4fff8b812ea15ff395fc
Source dataset
uspto-grants-1976_01
Patent number
US03931302

Reaction notes

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