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

HRID 2094319Notes

Reaction equation

HRID 2094319 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-7d3b973fd6a041da8dbd4b95592da6e9
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Reaction notes

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