Реакция #1178421

Уравнение реакции

acetic acid

nitrocyclohexane

sodium methoxide

3,5-dichlorobenzaldehyde

→

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

Растворители

water

methanol

Условия реакции

Обработка

1. 1
   Температураcooled in an ice bath
2. 2
   Температураcooled in an ice bath
3. 3
   workup.STIRRINGThe mixture was stirred over the weekend
4. 4
   Другоеrecooled in an ice bath
5. 5
   Экстракцияextracted with ether (2×75 mL)
6. 6
   ПромывкаThe combined ether extracts were washed with water (100 mL)
7. 7
   Сушкаdried over MgSO4
8. 8
   ДругоеRemoval 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
    ПромывкаFlash chromatography on silica gel, eluting with a 0-100% ether in hexanes gradient provided product of increased purity (ca. 70%)

Методика

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).

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