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Chemical Structure| 22002-17-1 Chemical Structure| 22002-17-1

Structure of 22002-17-1

Chemical Structure| 22002-17-1

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Product Details of [ 22002-17-1 ]

CAS No. :22002-17-1
Formula : C7H6Cl2O2
M.W : 193.03
SMILES Code : OC1=C(Cl)C=C(CO)C=C1Cl
MDL No. :MFCD06202847

Safety of [ 22002-17-1 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H315-H318-H335
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 22002-17-1 ]

* 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 [ 22002-17-1 ]

[ 22002-17-1 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 79-46-9 ]
  • [ 22002-17-1 ]
  • [ 2314-36-5 ]
  • [ 85628-45-1 ]
  • 2
  • [ 22002-17-1 ]
  • [ 2314-36-5 ]
YieldReaction ConditionsOperation in experiment
22% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; 2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CH2CI2, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77g, 22percent). LC-MS: tR = 0.82 min.
22% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; 2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CH2Cl2, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77 g, 22percent). LC-MS: tR=0.82 min.
22% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; 2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CHaCk, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77g, 22percent). LC-MS: tR = 0.82 min.
22% With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; at 20℃; 2,6-Dichloro-4-hydroxymethylphenol (3.56 g, 18.4 mmol) was dissolved in dioxane, and DDQ (4.19 g, 18.4 mmol) was added. The reaction mixture was stirred at rt overnight. The solvents were removed under reduced pressure. The residue was diluted with CH2Cl2, and the mixture was filtered. The filtrate was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Crystallization from EtOAc yielded the title compound (0.77 g, 22percent). LC-MS: tR = 0.82 min.

  • 3
  • [ 2314-36-5 ]
  • [ 22002-17-1 ]
  • 4
  • [ 3336-41-2 ]
  • [ 22002-17-1 ]
YieldReaction ConditionsOperation in experiment
96% With borane-THF; In tetrahydrofuran; at 0 - 20℃; for 13.25h; BH3 (1M in THF, 250 mL, 250 mmol) was added dropwise to a cooled sol. of <strong>[3336-41-2]3,5-dichloro-4-hydroxybenzoic acid</strong> (20 g, 96.6 mmol) in THF (200 mL) at 0 C. The resulting mixture was stirred at 0 C for 15 min., and then at rt for 13 h. The milky mixture was cooled to 0 C, and MeOH (150 mL), then water (100 mL), were added dropwise. The mixture was further stirred at 0 C for 15 min, and then at rt for 5 h. The mixture was then partially concentrated under reduced pressure. EtOAc (200 mL) and water (50 mL) were added to the residue, and the phases were shaken and separated. Theaq. phase was further extracted with EtOAc. The combined org. extracts were washed with brine, dried over MgSC^, filtered, and concentrated under reduced pressure. Purification by FC (CH2Cl2/CH3OH, 100:1) led to the title compound as a slightly beige solid (17.86 g, 96%). LC-MS: tR = 0.69 min.
96% BH3 (1M in THF, 250 mL, 250 mmol) was added dropwise to a cooled sol. of <strong>[3336-41-2]3,5-dichloro-4-hydroxybenzoic acid</strong> (20 g, 96.6 mmol) in THF (200 mL) at 0 C. The resulting mixture was stirred at 0 C. for 15 min, and then at rt for 13 h. The milky mixture was cooled to 0 C. and MeOH (150 mL), then water (100 mL), were added dropwise. The mixture was further stirred at 0 C. for 15 min, and then at rt for 5 h. The mixture was then partially concentrated under reduced pressure. EtOAc (200 mL) and water (50 mL) were added to the residue, and the phases were shaken and separated. The aq. phase was further extracted with EtOAc. The combined org. extracts were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by FC (CH2Cl2/CH3OH, 100:1) led to the title compound as a slightly beige solid (17.86 g, 96%). LC-MS: tR=0.69 min.
96% BH3 (1M in THF, 250 mL, 250 mmol) was added dropwise to a cooled sol. of <strong>[3336-41-2]3,5-dichloro-4-hydroxybenzoic acid</strong> (20 g, 96.6 mmol) in THF (200 mL) at 0 C. The resulting mixture was stirred at 0 C for 15 min, and then at rt for 13 h. The milky mixture was cooled to 0 C and MeOH (150 mL), then water (100 mL), were added dropwise. The mixture was further stirred at 0 C for 15 min, and then at rt for 5 h. The mixture was then partially concentrated under reduced pressure. EtOAc (200 mL) and water (50 mL) were added to the residue, and the phases were shaken and separated. The aq. phase was further extracted with EtOAc. The combined org. extracts were washed with brine, dried over MgSC>4, filtered, and concentrated under reduced pressure. Purification by FC (CH2Cl2/MeOH, 100:1) led to the title compound as a slightly beige solid (17.86 g, 96%). LC-MS: tR = 0.69 min.
96% BH3 (IM in THF, 250 mL, 250 mmol) was added dropwise to a cooled sol. of 3,5- dichloro-4-hydroxybenzoic acid (20 g, 96.6 mmol) in THF (200 mL) at 0 C. The resulting mixture was stirred at 0 C for 15 min., and then at rt for 13 h. The milky mixture was cooled to 0 C and MeOH (150 mL), then water (100 mL), were added dropwise. The mixture was further stirred at 0 C for 15 min., and then at rt for 5 h. The mixture was then partially concentrated under reduced pressure. EtOAc (200 mL) and water (50 mL) were added to the residue, and the phases were shaken and separated. The aq. phase was further extracted with EtOAc. The combined org. extracts were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by FC (CH2C12/CH3OH, 100:1) led to the title compound as a slightly beige solid (17.86 g, 96%). LC-MS: tR = 0.69 min.

 

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