Lithium hydroxide, monohydrate → 3-(4-Chloro-2-methylphenoxy)propionic acid

HRID 1369021Notes

Reaction equation

HRID 1369021 reaction equation
O[Li].O.[Cl:4][C:5]1[CH:18]=[CH:17][C:8]([O:9][CH2:10][CH2:11][C:12]([O:14]CC)=[O:13])=[C:7]([CH3:19])[CH:6]=1>O.C1COCC1>[Cl:4][C:5]1[CH:18]=[CH:17][C:8]([O:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])=[C:7]([CH3:19])[CH:6]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 12375248HCID 12375248, compound

Product 1

HCID 619053-(4-Chloro-2-methylphenoxy)propionic acidYield 35.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH.H2O (0.50 g; 12 mmol) in water (10 mL) was added to a solution of ethyl 3-(4-chloro-2-methylphenoxy)propionate (1.98 g; 8.15 mmol; from step (i) above) in THF (20 mL). The reaction mixture was stirred at room temperature overnight, THF was evaporated and the water phase was washed with ether. The resultant solution was acidified with HCl (2M), whereafter a solid material precipitated. The product was filtered and air-dried yielding 0.62 g (35%) of the sub-title compound.

Workup

  1. customTHF was evaporated
  2. washthe water phase was washed with ether
  3. customprecipitated
  4. filtrationThe product was filtered
  5. customair-dried

Sources & evidence

ORD record
ord-8888693e9dbf487f95f2fe18f4db937b
Source dataset
uspto-grants-2003_06
Patent number
US06576657B2

Reaction notes

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