تفاعل #1178421

معادلة التفاعل

acetic acid

nitrocyclohexane

sodium methoxide

3,5-dichlorobenzaldehyde

→

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

المذيبات

water

methanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled in an ice bath
2. 2
   درجة الحرارةcooled in an ice bath
3. 3
   workup.STIRRINGThe mixture was stirred over the weekend
4. 4
   أخرىrecooled in an ice bath
5. 5
   استخلاصextracted with ether (2×75 mL)
6. 6
   غسيلThe combined ether extracts were washed with water (100 mL)
7. 7
   تجفيفdried over MgSO4
8. 8
   أخرىRemoval 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
    غسيلFlash chromatography on silica gel, eluting with a 0-100% ether in hexanes gradient provided product of increased purity (ca. 70%)

الإجراء التجريبي

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).

المصدر