Reaction #1178421

Reaction equation

acetic acid

nitrocyclohexane

sodium methoxide

3,5-dichlorobenzaldehyde

→

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

Solvents

water

methanol

Conditions

Workup

1. 1
   Temperaturecooled in an ice bath
2. 2
   Temperaturecooled in an ice bath
3. 3
   workup.STIRRINGThe mixture was stirred over the weekend
4. 4
   Otherrecooled in an ice bath
5. 5
   Extractionextracted with ether (2×75 mL)
6. 6
   WashThe combined ether extracts were washed with water (100 mL)
7. 7
   Dryingdried over MgSO4
8. 8
   OtherRemoval 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
    WashFlash chromatography on silica gel, eluting with a 0-100% ether in hexanes gradient provided product of increased purity (ca. 70%)

Procedure

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).

Source