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

HRID 460289ノート

反応式

HRID 460289 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d5791ae395814665b1e6dc8ebf1efea6
出典データセット
uspto-grants-2007_03
特許番号
US07196108B2

反応ノート

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