Acetic Acid → HCID 59713390, compound

HRID 1091239Notes

Reaction equation

HRID 1091239 reaction equation
C[O-].[Na+].[N+:4]([CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)([O-:6])=[O:5].[Cl:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([Cl:22])[CH:21]=1)[CH:17]=[O:18].C(O)(=O)C>CO.O>[Cl:13][C:14]1[CH:15]=[C:16]([CH:17]([C:7]2([N+:4]([O-:6])=[O:5])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[OH:18])[CH:19]=[C:20]([Cl:22])[CH:21]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14285NitrocyclohexaneHCID 357463,5-DichlorobenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 59713390HCID 59713390, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

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).

Workup

  1. temperaturecooled in an ice bath
  2. temperaturecooled in an ice bath
  3. stirringThe mixture was stirred over the weekend
  4. customrecooled in an ice bath
  5. extractionextracted with ether (2×75 mL)
  6. washThe combined ether extracts were washed with water (100 mL)
  7. dry with materialdried over MgSO4
  8. customRemoval of the solvent
  9. waitleft crude (3,5-dichloro-phenyl)-(1-nitro-cyclohexyl)-methanol (8.93 g) as a yellow oil
  10. washFlash chromatography on silica gel, eluting with a 0-100% ether in hexanes gradient provided product of increased purity (ca. 70%)

Sources & evidence

ORD record
ord-efd9a7c3294e4116a92d3eea12526b10
Source dataset
uspto-grants-2012_03
Patent number
US08129355B2

Reaction notes

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