2,6-Dibromo-3,5-dihydroxy-4[(dimethylamino) methylene]-benzoic Acid → 3,5-Dihydroxy-4-methylbenzoic Acid

HRID 1692614노트

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HRID 1692614 반응식
Br[C:2]1[CH:10]([OH:11])[C:9](=[CH:12]N(C)C)[C:8]([OH:16])=[C:7](Br)[C:3]=1[C:4]([OH:6])=[O:5]>[OH-].[Na+].[Ni]>[OH:11][C:10]1[CH:2]=[C:3]([CH:7]=[C:8]([OH:16])[C:9]=1[CH3:12])[C:4]([OH:6])=[O:5]

참가 물질

4

반응물 1

HCID 866432502,6-Dibromo-3,5-dihydroxy-4[(dimethylamino) methylene]-benzoic Acid

생성물 1

HCID 27480453,5-Dihydroxy-4-methylbenzoic Acid수율 70%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 14798Sodium Hydroxide용매

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온도
25 °C

실험 절차

To a stirred solution of 2,6-Dibromo-3,5-dihydroxy-4[(dimethylamino) methylene]-benzoic Acid (1 mmol) in 2.5 mL of 3 N NaOH under nitrogen was added 0.345 g of Raney nickel in portions over a period of 1 h. The mixture was then stirred at 25° C. for about 12 h and filtered. The filter cake was washed with water (2×5 mL), and the combined filtrates were acidified to a pH of 1 with concentrated HCl to give a pale yellow or light purple solution. The solution was extracted with ethyl acetate, and the combined organic extracts were washed with saturated NaCl solution (2×0.2 mL), dried over sodium sulphate and evaporated by a rotatory evaporator to give 3,5-Dihydroxy-4-methylbenzoic Acid (70%) as a white solid: 1H NMR (DMSO-d6) δ 6.90 (s, 2H), 1.95 (s, 3H).

후처리

  1. filtrationfiltered
  2. washThe filter cake was washed with water (2×5 mL)
  3. customto give a pale yellow or light purple solution
  4. extractionThe solution was extracted with ethyl acetate
  5. washthe combined organic extracts were washed with saturated NaCl solution (2×0.2 mL)
  6. dry with materialdried over sodium sulphate
  7. customevaporated by a rotatory evaporator

출처 및 근거

ORD 기록
ord-a21c5f64929b4c32b1396deb9ccc317f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158623B2

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