Iodine → 5-Iodo-2,4-dimethylbenzoic acid

HRID 541189

반응식

HRID 541189 반응식
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[I:12]([O-])(=O)(=O)=O.[Na+].II.S(=O)(=O)(O)O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(O)(=O)C.O>[I:12][C:8]1[C:9]([CH3:11])=[CH:10][C:2]([CH3:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

참가 물질

8

반응물 5

HCID 807IodineHCID 1118Sulfuric AcidHCID 118972,4-Dimethylbenzoic acidHCID 24477Sodium ThiosulfateHCID 23667635Sodium periodate

생성물 1

HCID 230918755-Iodo-2,4-dimethylbenzoic acid수율 162.9%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

A solution of 2,4-dimethylbenzoic acid (20 g, 133.18 mmol, 1.00 equiv), sodium periodate (14.27 g, 66.72 mmol, 0.50 equiv), iodine (37.25 g, 146.76 mmol, 1.10 equiv), and sulfuric acid (1.96 g, 19.98 mmol, 0.15 equiv) in acetic acid (150 mL) was stirred at 110° C. in an oil bath. After 6 h, the reaction mixture was allowed to reach ambient temperature and was then diluted with 1.2 L of water. To this was carefully added 800 mL of aq Na2S2O3 (aq., sat.). The resulting solids were collected by filtration, dissolved in 1.2 L of ethyl acetate, and washed with 1×300 mL of Na2S2O3 (aq., sat.) followed by 1×400 mL of brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure. The crude residue was re-crystallized from ethanol:H2O (2:1) to yield 30 g (82%) of the title compound as a white solid.

후처리

  1. customto reach ambient temperature
  2. filtrationThe resulting solids were collected by filtration
  3. dissolutiondissolved in 1.2 L of ethyl acetate
  4. washwashed with 1×300 mL of Na2S2O3 (aq., sat.)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe crude residue was re-crystallized from ethanol:H2O (2:1)

출처 및 근거

ORD 기록
ord-71925f748cbd4e50a6e93e09ecaac4a8
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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