ChemicalBook CAS DataBase List 2,4,6-TRICHLOROPHENOXYACETIC ACID

2,4,6-TRICHLOROPHENOXYACETIC ACID synthesis

14synthesis methods

Product Name:2,4,6-TRICHLOROPHENOXYACETIC ACID
CAS Number:575-89-3
Molecular formula:C8H5Cl3O3
Molecular Weight:255.48

105-39-5 Synthesis

105-39-5
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$10.00/5g

88-06-2
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575-89-3
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$64.00/5g

Yield: 83%

Reaction Conditions:

Stage #1:chloroacetic acid ethyl ester;2,4,6-Trichlorophenol with potassium carbonate;potassium iodide in N,N-dimethyl-formamide for 0.0666667 h;Microwave irradiation;
Stage #2: with sodium hydroxide in N,N-dimethyl-formamide for 0.0833333 h;Microwave irradiation;

Steps:

2.2.1. Synthesis of HCPA, HMCPA, and HTCPA
General procedure: The three ligands were prepared by microwave synthesis in the following route (Scheme 1). A mixture of 3-chlorophenol (5 mmol) for 1, 4-chloro-2-methylphenol (5 mmol) for 2 or 2,4,6-trichlorophenol (5 mmol) for 3, ethyl chloroacetate (5 mmol), K2CO3 (5 mmol), KI (1 mmol), PEG-600 (0.5 mmol), and DMF(2 mL) was irradiated in a microwave oven under 200 W for 4 min, then 5 mL of NaOH (2 M) was added and irradiated 5 min at 500 W. After cooling to room temperature, the resulting aqueous solution was acidified (pH 6) by the addition of a 1 M HCl solution under vigorous stirring. Column chromatography provided three white solids. ¹H NMR (DMSO/TMS, 500 MHz, ppm): HCPA (Yield: 88%) δ 13.17 (s, 1H), 7.40 (t, J = 8.3 Hz, 1H), 7.14-7.07 (m, 2H), 7.02-6.97 (m, 1H), 4.83 (s, 2H). HMCPA (Yield: 86%) δ 13.04 (s, 1H), 7.22 (d, J = 2.2 Hz, 1H), 7.15 (dt, J = 10.3, 5.1 Hz, 1H), 6.83 (d, J = 8.8 Hz, 1H), 4.70 (d, J = 12.1 Hz, 2H), 2.18 (s, 3H). HTCPA (Yield: 83%) δ 13.25 (s, 1H), 7.81 (s, 2H), 4.68 (s, 2H).

References:

Xu, Xiuling;Yan, Saisai;Hu, Fan;Zhao, Wei;Shuai, Qi [Journal of Coordination Chemistry,2016,vol. 69,# 3,p. 541 - 550]