反応 #1702073

ord-a8b5dcdd27e04124891270579f140223

反応方程式

O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].O=[N+]([O-])[O-].[Ce+4].[NH4+].[NH4+]
CAN
O=[N+]([O-])[O-].[Ce].[NH4+]
cerium ammonium nitrate
Cc1ccc2c(c1)C(C)(C)CCC2(C)C
5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-methylnaphthalene
O=[N+]([O-])[O-].[Ce].[NH4+]
cerium ammonium nitrate
CC1(C)CCC(C)(C)c2cc(C=O)ccc21
5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthaldehyde

反応条件

温度
100°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    抽出extracted by ethyl acetate
  2. 2
    洗浄The organic layer was washed by water
  3. 3
    乾燥a saturated sodium hydrogen carbonate aq. solution and a saturated saline solution, dried over magnesium sulfate
  4. 4
    濃縮concentrated under reduced pressure
  5. 5
    その他The crude product was purified by silica gel chromatography

実験手順

The synthesis process is as set forth in the chemical reaction formula below. The CAN in the reaction path stands for cerium ammonium nitrate. To 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-methylnaphthalene (b) (202 mg, 1.00 mol) were added acetic acid (8.2 mL) and cerium ammonium nitrate (2.40 g, 4.37 mol) followed by stirring at 100° C. for 1 hour. The reaction solution was poured into ice water and extracted by ethyl acetate. The organic layer was washed by water, a saturated sodium hydrogen carbonate aq. solution and a saturated saline solution, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using hexane/ethyl acetate (15/1) as an elution solvent. The yield was 106 mg (49%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08765719B2uspto-grants-2014_07