Lithium Hydroxide → 3-Chloro-4-(4-methyl-2-oxo-oxazolidin-3-yl)-benzoic acid

HRID 1629888Notes

Reaction equation

HRID 1629888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]([CH3:18])[CH2:16][O:15][C:14]1=[O:19])[C:5]([O:7]CC)=[O:6].[OH-].[Li+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]([CH3:18])[CH2:16][O:15][C:14]1=[O:19])[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67048447Ethyl 3-chloro-4-(4-methyl-2-oxo-oxazolidin-3-yl)-benzoate

Product 1

HCID 667314913-Chloro-4-(4-methyl-2-oxo-oxazolidin-3-yl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.90 g (3.17 mmol) ethyl 3-chloro-4-(4-methyl-2-oxo-oxazolidin-3-yl)-benzoate are stirred for 1 hour in 50 ml of methanol with 10 ml 1-molar aqueous lithium hydroxide solution at ambient temperature. The mixture is then evaporated down to 20 ml i. vac., acidified with conc. hydrochloric acid and extracted with ethyl acetate. The combined organic phases are washed with sat. sodium chloride solution, dried over sodium sulphate and evaporated down i. vac. The residue is crystallised from a little diethyl ether and suction filtered.

Workup

  1. customThe mixture is then evaporated down to 20 ml i
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed with sat. sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated down i
  6. customThe residue is crystallised from a little diethyl ether and suction
  7. filtrationfiltered

Sources & evidence

ORD record
ord-9f5a481de27b4c05a0e60a9eb47042e7
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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