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

HRID 28258

Reaction equation

HRID 28258 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][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].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][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:26][OH:27])#[N:19]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 1049PyridineHCID 74601Benzyltriethylammonium hydroxideHCID 12343263alpha-n-Octyl-2,4-dichlorobenzyl cyanide

Product 1

HCID 233398862-Cyano-2-(2,4-dichlorophenyl)decan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cold stirred solution of α-n-octyl-2,4-dichlorobenzyl cyanide (40 g., 0.14 mole) in 250 ml. of pyridine containing a suspension of paraformaldehyde (21 g., 0.7 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 2 liters 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 40 g. of a thick oil.

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 40 g

Sources & evidence

ORD record
ord-70f27aa1486349138358461df4b145a3
Source dataset
uspto-grants-1980_09
Patent number
US04225723

Linked notes

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