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

HRID 614069

Reaction equation

HRID 614069 reaction equation
[CH2:1]([CH:5]([C:14]#[N:15])[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13])[CH2:2][CH2:3][CH3:4].[CH2:16]=[O:17].[OH-].C([N+](CC)(CC)CC)C1C=CC=CC=1>N1C=CC=CC=1>[C:14]([C:5]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13])([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:16][OH:17])#[N:15]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 74601Benzyltriethylammonium hydroxideHCID 123432572-(2,4-Dichlorophenyl)hexane nitrile

Product 1

HCID 233399042-Cyano-2-(2,4-dichlorophenyl)hexan-1-ol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice cold stirred solution of α-n-butyl-2,4-dichlorobenzylcyanide (5g., 0.02 mole) in 20 ml. of pyridine containing a suspension of paraformaldehyde (2.4g., 0.08 mole) is added 1 ml. of benzyl triethylammonium hydroxide. The mixture is stirred under nitrogen at room temperature for 16 hours. The reaction mixture is poured into 300 ml. 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 5.6g. of a thick oil, which is identified by nmr.

Workup

  1. additionis added 1 ml
  2. additionThe reaction mixture is poured into 300 ml
  3. extractionof water and extracted with ether
  4. washThe combined ether extracts are washed with water, saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is evaporated
  7. customto give 5.6g

Sources & evidence

ORD record
ord-312fc36fd690474e82e603111cb5a6d3
Source dataset
uspto-grants-1979_03
Patent number
US04143137

Linked notes

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