Hydrochloric Acid → (3-Chloro-4-methylsulfanyl-phenyl)-oxo-acetic acid

HRID 1843010Notes

Reaction equation

HRID 1843010 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[O:16])[C:11]([O:13]CC)=[O:12])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9].[OH-].[Na+].C(OCC)(=O)C.CCCCCC.Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[O:16])[C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[S:8][CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21226206Ethyl acetate hexaneHCID 53981255Ethyl 2-(3-chloro-4-(methylthio)phenyl)-2-oxoacetate

Product 1

HCID 12067649(3-Chloro-4-methylsulfanyl-phenyl)-oxo-acetic acidYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of ethyl 2-(3-chloro-4-(methylthio)phenyl)-2-oxoacetate (12 g, 0.49 mol) in toluene (120 mL, 10 times) was heated to 50° C. 3M NaOH solution (2.23 g, 1.2 eq) was added drop wise at 50° C. and the contents were allowed to reflux for 3 h at 60° C. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, Rf˜0.1). On completion of the reaction, toluene was distilled off and the residue obtained was taken in ice cold water. Then the contents were acidified with diluted HCl at 0° C. and allowed to stir for 1 h at room temperature. The precipitate was filtered and dried to yield 2-(3-chloro-4-(methylthio)phenyl)-2-oxoacetic acid as an yellow colored solid (10 g, 93%).

Workup

  1. distillationwas distilled off
  2. customthe residue obtained
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-c84b3b450d3440b498464aa750d9821b
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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