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ChemicalBook CAS DataBase List 2,4-Dichloro-3,5-dimethylphenol
133-53-9

2,4-Dichloro-3,5-dimethylphenol synthesis

4synthesis methods
2,4-Dichloro-3,5-dimethylphenol is obtained by reaction of 4-chloro-3,5-dimethylphenol with N-chloroacetamide in glacial acetic acid with concentrated HCl.
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Yield:88-04-0 75 %Chromat. ,5538-41-0 10 %Chromat. ,133-53-9 9 %Chromat.

Reaction Conditions:

with iron(III) chloride;sulfuryl dichloride;1,3-bis(methylthio)propane in dichloromethane at 20; for 4 h;regioselective reaction;Reagent/catalyst;

Steps:

4.2. Typical experimental procedure for the chlorination of m-xylenol

General procedure: Freshly distilled sulfuryl chloride (4.66 mL, 57.7mmol) was added slowly over 2 h, via a pressure equalizing dropping funnel, to a solution of m-xylenol (6.1 g, 50 mmol), FeCl3 (25mg, 0.154mmol) and an additive (30 mg) in DCM (25 mL) in a round bottomed flask (50mL). The mixture was stirred at room temperature for a further 2h and the reaction was quenched with water (20mL). The organic components were extracted with ether (3×30 mL). The ether layers were removed, combined and dried over MgSO4. The drying agent was filtered and the solvent was removed under reduced pressure. The crude product was weighed and then analyzed by quantitative GC in the presence of tetradecane as added internal standard.

References:

Smith, Keith;Al-Zuhairi, Ali J.;Elliott, Mark. C.;El-Hiti, Gamal A. [Journal of Sulfur Chemistry,2018,vol. 39,# 6,p. 607 - 621]

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