2,6-Dichlorophenol → HCID 136088167, compound

HRID 2282783Notes

Reaction equation

HRID 2282783 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N:14]([O-])=O.[Na+].[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:20]=1[OH:26]>O.Cl.[OH-].[K+]>[Cl:18][C:19]1[CH:24]=[C:23]([N:14]=[N:1][C:2]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH:22]=[C:21]([Cl:25])[C:20]=1[OH:26]

Participants

7

Reactant 3

HCID 68992,6-DichlorophenolHCID 27248222-Aminoterephthalic acidHCID 23668193Sodium Nitrite

Product 1

HCID 136088167HCID 136088167, compoundYield 20.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent3×HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

2-Aminoterephtalic acid (0.500 g, 2.76 mmol) was dissolved in hot mixture of 30 mL of water and 10 mL of conc. HCl. The solution was cooled in ice/NaCl bath to 0° C. giving a suspension of HCl salt. The solution of sodium nitrite (0.230 g, 3.33 mmol in 10 mL of water) was added dropwise to the suspension of ammonium salt, maintaining the temperature below +5° C. The resulting solution was stirred for 20 min and added dropwise to the solution of 2,6-dichlorophenol (0.450 g, 2.76 mmol) in 80 mL of 2M KOH, cooled in ice/water bath. The reaction mixture was stirred for 2 hrs in ice/water bath and then acidified with 10% HCl to pH 2-3 and extracted with ethyl acetate (3×30 mL). The combined extract was washed with brine (30 mL), dried over Na2SO4 and evaporated. The crude product was purified by column chromatography on silica gel using 60:15:1 chloroform-methanol-acetic acid as an eluant to give phenol 6 as a orange solid (0.200 g, 20%).

Workup

  1. customgiving
  2. temperaturemaintaining the temperature below +5° C
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. extractionThe combined extract
  5. washwas washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe crude product was purified by column chromatography on silica gel using 60:15:1 chloroform-methanol-acetic acid as an eluant

Sources & evidence

ORD record
ord-bf9d2bc86a764ac094fb6a33bd16e569
Source dataset
uspto-grants-2015_09
Patent number
US09140706B2

Reaction notes

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