Formaldehyde → 2-Cyano-2-(2-pyridyl)-2-phenyl ethanol

HRID 28267

Reaction equation

HRID 28267 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH2:22]=[O:23].[OH-].C([N+](CC)(CC)CC)C1C=CC=CC=1>O>[C:8]([C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:22][OH:23])#[N:9]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1049PyridineHCID 74601Benzyltriethylammonium hydroxideHCID 95510alpha-Phenyl-2-pyridineacetonitrile

Product 1

HCID 233399272-Cyano-2-(2-pyridyl)-2-phenyl ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cold stirred solution of phenyl-2-pyridyl acetonitrile* (50 g., 0.26 mole) in 350 ml. of pyridine containing a suspension of paraformaldehyde (31 g., 1.0 mole) is added 1 ml. of benzyl triethylammonium hydroxide. The mixture is stirred under nitrogen at room temperature for 24 hours. The reaction mixture is poured into water and extracted with ether. The combined ether extracts are washed with water, saturated sodium chloride solution and dried over magnesium sulfate. The solvent is evaporated to give a thick oil 58 g, which is identified by nmr.

Workup

  1. additionis added 1 ml
  2. extractionextracted with ether
  3. washThe combined ether extracts are washed with water, saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is evaporated

Sources & evidence

ORD record
ord-431ebc92c4514c90b13adef98fe73719
Source dataset
uspto-grants-1980_09
Patent number
US04225723

Linked notes

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