2-(2,4-DICHLOROPHENYLTHIO)ACETIC ACID synthesis
- Product Name:2-(2,4-DICHLOROPHENYLTHIO)ACETIC ACID
- CAS Number:7720-41-4
- Molecular formula:C8H6Cl2O2S
- Molecular Weight:237.1
Yield:7720-41-4 83.5%
Reaction Conditions:
with sodium thiophenolate;sodium hydroxide for 5 h;
Steps:
4.5 2-Arylsulfanylpropionic (6a, c, e) and2-arylsulfanylacetic (6b, d, f) acids:general procedure
General procedure: An appropriate thiophenol 5 (0.0025 mol) and 20%aqueous sodium hydroxide solution (1 mL for liquidthiophenols: 2,4-dichlorothiophenol (5a) and 4-chloro-2-methylthiophenol (5b), or 2-3 mL for solid thiophenol:2,4,5-trichlorothiophenol (5c)) were placed in aflask. A solution of a sodium salt of 2-chloropropionicacid (3a) or chloroacetic acid (3b) was prepared separately.Compound 3a or 3b (0.0025 mol) was added tothe 20% aqueous sodium hydroxide solution (1 mL). The resulting solution of the sodium salt of the acid wasadded to a solution of sodium thiophenolate. A solution(in the case of liquid thiophenols) or a suspension(for a solid 2,4,5-trichlorothiophenol) was heated toT = 125-130°C with magnetic stirring for 5 h. The reactionmixture was allowed to cool to room temperature andtransferred with water (15-20 mL) to a beaker. The solution(pH = 11) was acidified with concentrated hydrochloricacid to pH = 2 (1-2 mL depending on the amount ofsodium hydroxide used). The resulting suspension wasextracted with methylene chloride (3 × 15 mL). The methylenechloride layers were dried over anhydrous magnesiumsulfate. Removal of drying agent and evaporation of themethylene chloride under reduced pressure afforded thecrude product (approx. 0.5 g), which was crystallized frombenzene (1.5-2 mL) to give pure thiophenoxy acids.
References:
Zakrzewski, Jerzy;Huras, Bogumi?a;Kie?czewska, Anna;Krawczyk, Maria [Zeitschrift fur Naturforschung, B: Chemical Sciences,2018,vol. 73,# 12,p. 1005 - 1013]
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