反应 #1178421

反应方程式

acetic acid

nitrocyclohexane

sodium methoxide

3,5-dichlorobenzaldehyde

→

(3,5-dichloro-phenyl)-(1-nitro-cyclohexyl)-methanol

溶剂

water

methanol

反应条件

后处理

1. 1
   温度cooled in an ice bath
2. 2
   温度cooled in an ice bath
3. 3
   workup.STIRRINGThe mixture was stirred over the weekend
4. 4
   其他recooled in an ice bath
5. 5
   萃取extracted with ether (2×75 mL)
6. 6
   洗涤The combined ether extracts were washed with water (100 mL)
7. 7
   干燥dried over MgSO4
8. 8
   其他Removal of the solvent
9. 9
   workup.WAITleft crude (3,5-dichloro-phenyl)-(1-nitro-cyclohexyl)-methanol (8.93 g) as a yellow oil
10. 10
    洗涤Flash chromatography on silica gel, eluting with a 0-100% ether in hexanes gradient provided product of increased purity (ca. 70%)

实验过程

25% sodium methoxide solution (24.9 mmol, 5.7 mL) was diluted with methanol (40 mL), cooled in an ice bath, and nitrocyclohexane was added dropwise over 10 min. The mixture was stirred for 30 min, cooled in an ice bath, and solid 3,5-dichlorobenzaldehyde was added. The mixture was stirred over the weekend, recooled in an ice bath, and treated with 2 mL of glacial acetic acid. The mixture was poured into water (125 mL) and extracted with ether (2×75 mL). The combined ether extracts were washed with water (100 mL) and dried over MgSO4. Removal of the solvent left crude (3,5-dichloro-phenyl)-(1-nitro-cyclohexyl)-methanol (8.93 g) as a yellow oil. Flash chromatography on silica gel, eluting with a 0-100% ether in hexanes gradient provided product of increased purity (ca. 70%). 1H NMR (500 MHz, CDCl3) δ (ppm): 7.35 (s, 1H), 7.19 (s, 2H), 4.90 (s, 1H), 0.9-1.8 (m, 10H).

来源