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

HRID 2222542Notes

Reaction equation

HRID 2222542 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-8848c0efed4548c38d247482c1a5d1aa
Source dataset
uspto-grants-2008_05
Patent number
US07371743B2

Reaction notes

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