Chromate → 5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-benz[f]indan-2-one

HRID 1017161

反応式

HRID 1017161 の反応式
[CH3:1][C:2]1([CH3:17])[C:14]2[C:6](=[CH:7][C:8]3[CH2:9][CH2:10][CH2:11][C:12]=3[CH:13]=2)[C:5]([CH3:16])([CH3:15])[CH2:4][CH2:3]1.[Cr]([O-])([O-])(=O)=[O:19]>C(O)(=O)C>[CH3:15][C:5]1([CH3:16])[C:6]2[C:14](=[CH:13][C:12]3[CH2:11][C:10](=[O:19])[CH2:9][C:8]=3[CH:7]=2)[C:2]([CH3:17])([CH3:1])[CH2:3][CH2:4]1

参加物

4

反応物 2

HCID 24461ChromateHCID 184028515,5,8,8-Tetramethyl-5,6,7,8-tetrahydrobenz(f)indane

生成物 1

HCID 184028485,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-benz[f]indan-2-one収率 94.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
70 °C

実験手順

A round bottom flask fit with a mechanical stirrer, condenser, thermometer, addition funnel, and nitrogen inlet was charged with 5,5,8,8-tetramethyl-5,6,7,8-tetrahydrobenz(f)indane (43.0 g, 0.0.19 mol) and 84 mL glacial acetic acid and heated to 70° C. While stirring chromate (56.7 g, 0.57 mol, Aldrich) was added slowly maintaining the temperature at about 110° C. After complete addition (30 minutes) the reaction was allowed to cool to room temperature for an additional 2½ hours. The reaction was quenched with 5% HCl/ice and extracted with diethyl ether. The combined ether extracts were washed with water and dried over anhydrous magnesium sulfate. Removal of the solvents by rotary evaporation gave 43.0 g of greenish solids which were washed with chilled acetone to give 16.0 g (98% pure by GC) of solids. The acetone wash was concentrated to give 15.0 g of more solids which were washed with hexane to give 8.7 g (79% pure by GC) of solids. The 16.0 g solids from the acetone wash and 8.7 g solids from the hexane wash were combined to give the crude 5,5,8,8-tetramethyl-5,6,7,8-tetrahydrobenz(f)indan-2one (total of 24.7 g). 1HNMR (CDCl3, 500 MHz) 6 7.75 (s, 1H); 7.43 (s, 1H); 3.08 (t, J=3.5 Hz, 2H); 2.66 (t, J=6 Hz, 2H); 1.71 (s, 4H); 1.32 (s, 6H); 1.30 (s, 6H).

後処理

  1. additionA round bottom flask fit with a mechanical stirrer, condenser, thermometer, addition funnel, and nitrogen inlet
  2. additionwas added slowly
  3. temperaturemaintaining the temperature at about 110° C
  4. additionAfter complete addition (30 minutes) the reaction
  5. temperatureto cool to room temperature for an additional 2½ hours
  6. customThe reaction was quenched with 5% HCl/ice
  7. extractionextracted with diethyl ether
  8. washThe combined ether extracts were washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customRemoval of the solvents
  11. customby rotary evaporation

出典と根拠

ORDレコード
ord-ec4a9638af654b88bc3e5f305db1951e
出典データセット
uspto-grants-2002_11
特許番号
US06479424B1

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