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Chemical Structure| 59595-92-5 Chemical Structure| 59595-92-5

Structure of 59595-92-5

Chemical Structure| 59595-92-5

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Product Details of [ 59595-92-5 ]

CAS No. :59595-92-5
Formula : C7H3Cl3O2
M.W : 225.46
SMILES Code : O=C(Cl)C1=CC(Cl)=C(O)C(Cl)=C1
MDL No. :MFCD28099713

Safety of [ 59595-92-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314-H290
Precautionary Statements:P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 59595-92-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 59595-92-5 ]

[ 59595-92-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 3336-41-2 ]
  • [ 59595-92-5 ]
YieldReaction ConditionsOperation in experiment
62% With thionyl chloride; at 20℃; for 37h;Reflux; <strong>[3336-41-2]3,5-dichloro-4-hydroxybenzoic acid</strong> (800 mg, 3.86 mmol) was dissolved in SOCl2 (10.0 mL) and the reaction mixture stirred at RT (16 h) and then heated to reflux (5 h). Next, SOCl2 was removed in vacuo and azeotroped twice with toluene to give a mixture of product and starting material. The crude compound was dissolved in SOCl2 (8.0 mL) and refluxed (16 h). The SOCl2 was removed in vacuo and azeotroped twice with toluene to give 78 (0.540 g, 2.40 mmol, 62percent) as a brown solid. 1H- NMR (400 MHz) CDC13: 8.07 (s, 2 H), 6.59 (bs, 1H); 13C-NMR (100 MHz) CDC13: 165.5, 153.7, 131.5 126.4, 121.8.
With thionyl chloride; In 1,2-dimethoxyethane; at 80℃; Step 1 Production of 3,5-dichloro-4-hydroxybenzoyl chloride 1,2-Dimethoxyethane (30 mL) was added to <strong>[3336-41-2]3,5-dichloro-4-hydroxybenzoic acid</strong> (1.242 g) to dissolve same by heating the mixture to 80° C. Thionyl chloride (0.57 mL) was added, and the mixture was stirred overnight at 80° C. The reaction mixture was concentrated under reduced pressure, azeotroped with toluene, and dried to give the title compound (1.358 g) as a white solid.
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20℃; for 1.58333h;Inert atmosphere; A screw top test tube equipped with a magnetic stirring bar was charged with <strong>[3336-41-2]3,5-dichloro-4-hydroxybenzoic acid</strong> (57.8 mg,0.279 mmol) and anhydrous dichloromethane (0.56 mL). To the solution were added oxalyl chloride (36 muL, 0.42 mmol) and N,N-dimethylformamide (DMF) (2.0 muL, 0.026 mmol) at 0°C. After the reaction mixture was stirred at 0°C for 5 min, the mixture was allowed to warm to room temperature and the solution was stirred for 1.5 h. The mixture was concentrated under reduced pressure to afford 3,5-dichloro-4-hydroxybenzoyl chloride as a yellow solid, which was used to the next reaction without further purification.
With thionyl chloride; In 1,2-dimethoxyethane; at 24 - 80℃; for 8 - 22h;Product distribution / selectivity; Step 1 Production of 3,5-dichloro-4-hydroxybenzoyl chloride 1,2-Dimethoxyethane (30 mL) was added to <strong>[3336-41-2]3,5-dichloro-4-hydroxybenzoic acid</strong> (1.242 g) to dissolve the same by heating the mixture to 80° C. Thionyl chloride (0.57 mL) was added, and the mixture was stirred overnight at 80° C. The reaction mixture was concentrated under reduced pressure, azeotroped with toluene, and dried to give the title compound (1.358 g) as a white solid. Step 2 Production of 3,5-dichloro-4-hydroxybenzoyl chloride Under nitrogen atmosphere, 1,2-dimethoxyethane (0.80 L) was added to <strong>[3336-41-2]3,5-dichloro-4-hydroxybenzoic acid</strong> (100 g), and the mixture was stirred at 24° C. Thionyl chloride (74.7 g) was added, and the mixture was stirred at 60-70° C. for 22 hrs. The nitrogen flow was stopped, and the reaction mixture was concentrated under reduced pressure. 1,2-Dimethoxyethane (0.10 L) was added, and the reaction mixture was concentrated under reduced pressure. This operation was repeated twice to give a solution of the title compound in 1,2-dimethoxyethane (304 g). Step 2 Production of 3,5-dichloro-4-hydroxybenzoyl chloride Under nitrogen atmosphere, 1,2-dimethoxyethane (0.20 kL) was added to <strong>[3336-41-2]3,5-dichloro-4-hydroxybenzoic acid</strong> (25.0 kg), thionyl chloride (101 kg) was added, and the mixture was stirred at 50° C. for 8 hrs. The nitrogen flow was stopped, and the reaction mixture was concentrated under reduced pressure. Ethyl acetate (76 L) was added, and the reaction mixture was concentrated under reduced pressure (22-32° C.). This operation was repeated 4 times to give a solution of the title compound in ethyl acetate.

  • 2
  • [ 110-71-4 ]
  • [ 3336-41-2 ]
  • [ 59595-92-5 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; Step 1 Production of 3,5-dichloro-4-hydroxybenzoyl chloride 1,2-Dimethoxyethane (30 mL) was added to <strong>[3336-41-2]3,5-dichloro-4-hydroxybenzoic acid</strong> (1.242 g) to dissolve the same by heating the mixture to 80° C. Thionyl chloride (0.57 mL) was added, and the mixture was stirred overnight at 80° C. The reaction mixture was concentrated under reduced pressure, azeotroped with toluene, and dried to give the title compound (1.358 g) as a white solid.
 

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