Acetic Acid → HCID 54286268, compound

HRID 620327Notes

Reaction equation

HRID 620327 reaction equation
[OH-].[Na+].[N+](C1C=CC(C([O:12][C@@H:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]2[C@@H:19]([CH2:27][N+:28]([O-:30])=[O:29])[C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)=O)=CC=1)([O-])=O.C(O)(=O)C>C(O)C>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C@@H:19]([C@@H:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C@H:13]2[OH:12])[CH2:27][N+:28]([O-:30])=[O:29])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 86742923HCID 86742923, compound

Product 1

HCID 54286268HCID 54286268, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 490 ml (12.1 mmol) of sodium hydroxide in 40 ml of ethanol is added dropwise to a solution of 3.5 g (8.09 mmol) of rac-(1R*)-trans-2-[(R*)-4-chloro-α-(nitromethyl)benzyl]cyclohexyl p-nitrobenzoate in 80 ml of ethanol. The mixture is stirred at room temperature for 16 hours, treated with 1 ml of acetic acid and the solvent is distilled off in a water-jet vacuum. The residue is treated with water, whereupon the mixture is extracted twice with 100 ml of ether each time. The organic phase is washed with water, dried over magnesium sulphate and evaporated. The residue is chromatographed on a 30-fold amount of silica gel and there is obtained rac-(1R*)-trans-2-[(R*)-4-chloro-α-(nitromethyl)benzyl]cyclohexanol in the form of a yellowish oil.

Workup

  1. distillationthe solvent is distilled off in a water-jet vacuum
  2. additionThe residue is treated with water, whereupon the mixture
  3. extractionis extracted twice with 100 ml of ether each time
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residue is chromatographed on a 30-fold amount of silica gel

Sources & evidence

ORD record
ord-d525eb0732424b7bb4906a6e41dc77fc
Source dataset
uspto-grants-1989_04
Patent number
US04820734

Reaction notes

Loading…