Formaldehyde → 2-Cyano-2-(2,4-dichlorophenyl)-4-phenyl butan-1-ol

HRID 28266

Reaction equation

HRID 28266 reaction equation
[CH2:1]([CH:9]([C:18]#[N:19])[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH2:26]=[O:27].[OH-].C([N+](CC)(CC)CC)C1C=CC=CC=1>O>[C:18]([C:9]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])([CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:26][OH:27])#[N:19]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1049PyridineHCID 74601Benzyltriethylammonium hydroxideHCID 12391165alpha-Phenethyl-2,4-dichlorobenzyl cyanide

Product 1

HCID 233398832-Cyano-2-(2,4-dichlorophenyl)-4-phenyl butan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cold stirred solution of α-phenethyl-2,4-dichlorobenzyl cyanide (26.5 g., 0.09 mole) in 200 ml. of pyridine containing a suspension of paraformaldehyde (11 g., 0.35 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 1 liter of 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 25.4 g. of a thick oil, 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
  6. customto give 25.4 g

Sources & evidence

ORD record
ord-70506e1356f245978f86f3793a2ac26b
Source dataset
uspto-grants-1980_09
Patent number
US04225723

Linked notes

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