Formaldehyde → 2-Cyano-2-(4-chlorophenyl)propan-1-ol

HRID 614073

Reaction equation

HRID 614073 reaction equation
[CH3:1][CH:2]([C:10]#[N:11])[C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH2:18]=[O:19].[OH-].C([N+](CC)(CC)CC)C1C=CC=CC=1>O>[C:10]([C:2]([C:3]1[CH:4]=[CH:5][C:6]([Cl:9])=[CH:7][CH:8]=1)([CH3:1])[CH2:18][OH:19])#[N:11]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1049PyridineHCID 74601Benzyltriethylammonium hydroxideHCID 1027622-(4-Chlorophenyl)propiononitrile

Product 1

HCID 140328512-Cyano-2-(4-chlorophenyl)propan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cold stirred solution of α-methyl-4-chlorobenzyl cyanide* (50g., 0.3 mole) in 500 ml. of pyridine containing a suspension of paraformaldehyde (36g., 1.2 mole) is added 1 ml. of benzyl triethylammonium hydroxide. The mixture is stirred under nitrogen at room temperature for 72 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, 58.4g., 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 a thick oil, 58.4g

Sources & evidence

ORD record
ord-fa132888a26a4a03b93c0ec941ee0a04
Source dataset
uspto-grants-1979_03
Patent number
US04143137

Linked notes

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