Sulfanilic acid → 4-((3,5-Difluoro-4-hydroxyphenyl)diazenyl)benzenesulfonic acid

HRID 2043802

반응식

HRID 2043802 반응식
[S:1]([OH:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].[N:12]([O-])=O.[Na+].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[OH:24].[OH-].[K+]>O.Cl.O1CCOCC1>[F:16][C:17]1[CH:22]=[C:21]([N:12]=[N:9][C:6]2[CH:5]=[CH:4][C:3]([S:1]([OH:11])(=[O:10])=[O:2])=[CH:8][CH:7]=2)[CH:20]=[C:19]([F:23])[C:18]=1[OH:24]

참가 물질

8

반응물 4

HCID 8479Sulfanilic acidHCID 14797Potassium HydroxideHCID 943922,6-DifluorophenolHCID 23668193Sodium Nitrite

생성물 1

HCID 1357374494-((3,5-Difluoro-4-hydroxyphenyl)diazenyl)benzenesulfonic acid수율 79%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매2회HCID 962Water용매2회HCID 312751,4-Dioxane용매

실험 절차

Sulfanilic acid (0.767 g, 4.43 mmol) was dissolved in hot mixture of 20 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 (0.367 g, 5.32 mmol in 5 mL of water) was added dropwise to the suspension of ammonium salt, maintaining the temperature below +5° C. All solid dissolved and the resulting solution was stirred for 20 min. After that white precipitate formed again and the resulting suspension was added dropwise to the mixture of 2,6-difluorophenol (0.576 g, 4.43 mmol) in 10 mL of dioxane and KOH (10 g) in 15 mL of water, cooled in ice/water bath. The reaction mixture was stirred for 30 min in ice/water bath and then extracted with ethyl acetate (3×30 mL). The aqueous solution was acidified with 10% HCl to pH 2-3 and the formed yellow precipitate was collected, washed with water and dried in vacuum to give phenol 2 as a yellow powder (1.1 g, 79%).

후처리

  1. customgiving
  2. temperaturemaintaining the temperature below +5° C
  3. dissolutionAll solid dissolved
  4. customAfter that white precipitate formed again
  5. extractionextracted with ethyl acetate (3×30 mL)
  6. customthe formed yellow precipitate was collected
  7. washwashed with water
  8. customdried in vacuum

출처 및 근거

ORD 기록
ord-3c0800025e4f4cfd83086a3072658c37
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586743B2

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