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ChemicalBook CAS DataBase List Triclopyr
55335-06-3

Triclopyr synthesis

6synthesis methods
Acetic acid, (3,5,6-trichloro-2-pyridinyl)oxy-, ethyl ester

60825-27-6

Triclopyr

55335-06-3

The general procedure for the synthesis of 2-((3,5,6-trichloropyridin-2-yl)oxy)acetic acid from the compound (CAS: 60825-27-6) is as follows: in a reactor equipped with a mechanical stirrer, a thermometer casing, and a reflux condenser, 0.404 mol of trichloromethyl ethyl ester was added. Subsequently, an appropriate amount of water was added to prepare a 10% aqueous slurry. Next, 19.42 g (0.485 moles) of sodium hydroxide (NaOH) was added. The slurry was heated to 80°C and the reaction was maintained at this temperature for 3.5 hours. Upon completion of the reaction, the reaction mixture was cooled to room temperature. Then, 115 ml of 4% sodium hypochlorite (NaOCl) solution was added and the mixture was stirred for 30 minutes. After that, the reaction mixture was acidified with sulfuric acid to a pH of 1-2, at which point a white precipitate was produced. The precipitate was filtered and dried to give the final target product 2-((3,5,6-trichloropyridin-2-yl)oxy)acetic acid in 93% yield.

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Yield:55335-06-3 94.2%

Reaction Conditions:

Stage #1:methyl 2-[(3,5,6-trichloropyridin-2-yl)oxy]acetate with water;sodium hydroxide at 80 - 85; for 4 h;
Stage #2: with sulfuric acid in water; pH=1 - 2Product distribution / selectivity;

Steps:

4
In a reactor equipped with a mechanical stirrer, thermometer pocket and reflux condenser, 0.351 moles of triclopyr-methyl ester was taken. Water was added to make 10% aqueous slurry. 16.85 g (0.421 moles) of NaOH was added. The slurry was heated to 80-850C for four hours. The reaction mass was then cooled to room temperature. 70 ml H2O2 was added and mixture was stirred for 30 min. The reaction mass was then acidified to pH 1-2 with sulfuric acid to get white precipitate which was filtered and dried to obtain product in 94.2% yield

References:

EXCEL CROP CARE LIMITED;C C SHROFF RESEARCH INSTITUTE;AIMCO PESTICIDES LIMITED;SHROFF, Dipesh, Kantisen;SHROFF, Ashwin, Champraj;DAVE, Samir, Pradip WO2010/23679, 2010, A2 Location in patent:Page/Page column 6-7

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