Potassium Permanganate → 7-Bromo-3,3-dimethyl-2,3-dihydrobenzofuran-5-carboxylic acid

HRID 460289노트

반응식

HRID 460289 반응식
[Br:1][C:2]1[C:10]2[O:9][CH2:8][C:7]([CH3:12])([CH3:11])[C:6]=2[CH:5]=[C:4]([CH:13]=[O:14])[CH:3]=1.[O-:15][Mn](=O)(=O)=O.[K+]>CC(C)=O.O>[Br:1][C:2]1[C:10]2[O:9][CH2:8][C:7]([CH3:11])([CH3:12])[C:6]=2[CH:5]=[C:4]([C:13]([OH:15])=[O:14])[CH:3]=1

참가 물질

5

반응물 2

HCID 516875Potassium PermanganateHCID 184454227-Bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-carbaldehyde

생성물 1

HCID 220414067-Bromo-3,3-dimethyl-2,3-dihydrobenzofuran-5-carboxylic acid수율 64%

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

실험 절차

A solution of 7-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-carbaldehyde (14.61 g, 57.29 mmol) in acetone (80 mL) was added at room temperature to KMnO4 (9.05 g, 57.29 mmol) dissolved in water (200 mL). The reaction mixture was stirred at room temperature overnight filtered over celite then H2SO4 in water was added and the solution extracted with ethyl acetate. The organic layer was further washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated to give 9.9 g of 7-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-carboxylic acid (64%). 1H NMR (300 MHz; CDCl3): 1.40 (s, 6H), 4.44 (s, 2H), 7.79 (s, 1H), 8.13 (s, 1H). c. 7-bromo-3,3-dimethyl-2,3-dihydro-benzofuran-5-carbaldehyde.

후처리

  1. filtrationfiltered over celite
  2. additionH2SO4 in water was added
  3. extractionthe solution extracted with ethyl acetate
  4. washThe organic layer was further washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-d5791ae395814665b1e6dc8ebf1efea6
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196108B2

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