Lithium Hydroxide → 2-(4-chlorophenyl)-2-hydroxypropanoic acid

HRID 992453Notes

Reaction equation

HRID 992453 reaction equation
C([O:3][C:4](=[O:15])[C:5]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)([OH:7])[CH3:6])C.[OH-].[Li+]>O1CCCC1.O>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([C:5]([OH:7])([CH3:6])[C:4]([OH:15])=[O:3])=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 22888181HCID 22888181, compound

Product 1

HCID 100130442-(4-chlorophenyl)-2-hydroxypropanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.72 g of the 2-(4-chlorophenyl)-2-hydroxy propionic acid ethyl ester in 170 ml tetrahydrofurane is hydroysed at 0° C. with a solution of 30.5 ml 1N lithiumhydroxide in 19 ml water. When the reaction is complete, the reaction mixture is diluted with water, washed with diethyl ether, acidified with 1N HCl and extracted with ethyl acetate. The extracts are washed with brine, dried over sodium sulfate and evaporated to give 2-(4-chlorophenyl)-2-hydroxy propionic acid.

Workup

  1. washwashed with diethyl ether
  2. extractionextracted with ethyl acetate
  3. washThe extracts are washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-66ebd3e304814a6a93b3c2cd8d8d5741
Source dataset
uspto-grants-2002_10
Patent number
US06469005B1

Reaction notes

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