Benzene → 2-Cyano-2-(2,4-dichlorophenyl)hexyl methane sulfonate

HRID 614070Notes

Reaction equation

HRID 614070 reaction equation
[C:1]([C:3]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:4][OH:5])#[N:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20].C1C=CC=CC=1>C(N(CC)CC)C>[CH3:18][S:19]([O:5][CH2:4][C:3]([C:1]#[N:2])([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[Cl:17])[CH2:6][CH2:7][CH2:8][CH3:9])(=[O:21])=[O:20]

Participants

5

Reactant 3

HCID 241BenzeneHCID 31297Methanesulfonyl chlorideHCID 233399042-Cyano-2-(2,4-dichlorophenyl)hexan-1-ol

Product 1

HCID 233399252-Cyano-2-(2,4-dichlorophenyl)hexyl methane sulfonate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 2-cyano-2-(2,4-dichlorophenyl)hexan-1-ol (5.6g., 0.02 mole) and methane sulfonyl chloride (2.9g., 0.025 mole) in 200 ml. of benzene is added dropwise at 10° C., 2.8g. (0.027) of triethylamine. The reaction mixture is stirred at room temperature for 30 minutes and then heated on a steam bath for another 30 minutes. The precipitate formed is filtered and the filtrate is washed with dilute hydrochloric acid, water, saturated sodium bicarbonate solution, saturated sodium chloride solution and dried over magnesium sulfate. The solvent is evaporated to give 6.3g. of product.

Workup

  1. temperatureheated on a steam bath for another 30 minutes
  2. customThe precipitate formed
  3. filtrationis filtered
  4. washthe filtrate is washed with dilute hydrochloric acid, water, saturated sodium bicarbonate solution, saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is evaporated
  7. customto give 6.3g

Sources & evidence

ORD record
ord-d357bb61589c472ca22042a6a8f944c7
Source dataset
uspto-grants-1979_03
Patent number
US04143137

Reaction notes

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