반응 #1178421

반응 방정식

acetic acid

nitrocyclohexane

sodium methoxide

3,5-dichlorobenzaldehyde

→

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

용매

water

methanol

반응 조건

후처리

1. 1
   온도cooled in an ice bath
2. 2
   온도cooled in an ice bath
3. 3
   workup.STIRRINGThe mixture was stirred over the weekend
4. 4
   기타recooled in an ice bath
5. 5
   추출extracted with ether (2×75 mL)
6. 6
   세척The combined ether extracts were washed with water (100 mL)
7. 7
   건조dried over MgSO4
8. 8
   기타Removal 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
    세척Flash chromatography on silica gel, eluting with a 0-100% ether in hexanes gradient provided product of increased purity (ca. 70%)

실험 절차

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).

출처