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

HRID 616386Notes

Reaction equation

HRID 616386 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 -dichlorobenzyl cyanide (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 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. addition, 0.08 mole is added 1 ml
  2. additionThe reaction mixture 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-ae715a1f99aa47f889709b282b115d35
Source dataset
uspto-grants-1978_02
Patent number
US04073921

Reaction notes

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