Citric Acid → HCID 69915440, compound

HRID 1429344Notes

Reaction equation

HRID 1429344 reaction equation
C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([N+:34]([O-:36])=[O:35])=[C:19]([CH:21]([O:29][Si](C)(C)C)[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:20]=1>C(O)C.O>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([N+:34]([O-:36])=[O:35])=[C:19]([CH:21]([OH:29])[CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:20]=1

Participants

5

Reactant 2

HCID 311Citric AcidHCID 69915481HCID 69915481, compound

Product 1

HCID 69915440HCID 69915440, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Citric acid (0.51 g) was added to a solution of ethyl 4-(5-chloro-2-nitrophenyl)-4-(trimethylsilyloxy)butanoate (4.76 g) in ethanol (25 mL) and water (5 mL) and stirred at room temperature for 1.5 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. Subsequently, the solvent was distilled off and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1→10:1) to obtain 3.8 g of ethyl 4-(5-chloro-2-nitrophenyl)-4-hydroxybutanoate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationSubsequently, the solvent was distilled off
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1→10:1)

Sources & evidence

ORD record
ord-f0f0f67c24604c68bced1dfdaa343845
Source dataset
uspto-grants-2015_01
Patent number
US08940727B2

Reaction notes

Loading…