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

HRID 28254Notes

Reaction equation

HRID 28254 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].N1C=CC=CC=1.[CH2:22]=[O:23]>[OH-].C([NH+](CC)CC)C.C1C=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])[CH2:22][OH:23])#[N:15]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 1049PyridineHCID 123432572-(2,4-Dichlorophenyl)hexane nitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 23339897Benzene triethylammonium hydroxideSolvent

Procedure

To an ice cold stirred solution of a-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 benzene 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-1a195b73c5554f77aaf4b1251b91003e
Source dataset
uspto-grants-1980_09
Patent number
US04225723

Reaction notes

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