反应 #1702073

ord-a8b5dcdd27e04124891270579f140223

反应方程式

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

反应条件

温度
100°CELSIUS
详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    萃取extracted by ethyl acetate
  2. 2
    洗涤The organic layer was washed by water
  3. 3
    干燥a saturated sodium hydrogen carbonate aq. solution and a saturated saline solution, dried over magnesium sulfate
  4. 4
    浓缩concentrated under reduced pressure
  5. 5
    其他The crude product was purified by silica gel chromatography

实验过程

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%).

来源

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