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

HRID 1385991Notes

Reaction equation

HRID 1385991 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-be36d880a3594481bb8180a431a8e7fa
Source dataset
uspto-grants-2001_07
Patent number
US06265397B1

Reaction notes

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