Potassium Hydroxide → 3-Chloro-4-(methylthio)phenylacetic acid

HRID 1843011Notes

Reaction equation

HRID 1843011 reaction equation
O.NN.[Cl:4][C:5]1[CH:6]=[C:7]([C:13](=O)[C:14]([OH:16])=[O:15])[CH:8]=[CH:9][C:10]=1[S:11][CH3:12].[OH-].[K+].C(OCC)(=O)C.CCCCCC>O.C(OCC)(=O)C>[Cl:4][C:5]1[CH:6]=[C:7]([CH2:13][C:14]([OH:16])=[O:15])[CH:8]=[CH:9][C:10]=1[S:11][CH3:12]

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 12067649(3-Chloro-4-methylsulfanyl-phenyl)-oxo-acetic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 120676503-Chloro-4-(methylthio)phenylacetic acidYield 92.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To hydrazine hydrate (10 g, 5 eq) cooled at −50° C., 2-(3-chloro-4-(methylthio)phenyl)-2-oxoacetic acid (10 g, 0.04 mol) was added. The contents were initially warmed to room temperature and slowly heated to 80° C. Then KOH (5.59 g, 2.3 eq) was added portion wise at 80° C. and the overall reaction mass was allowed to reflux for 12-16 h at the same temperature. Progress of the reaction was monitored by TLC (50% ethyl acetate/hexane, Rf˜0.4). On completion of the reaction, the reaction contents were diluted with a mixture of water and ethyl acetate. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). Then the aqueous layer was acidified with diluted HCl and allowed to stir for 1 h at room temperature. The precipitate was filtered and dried to yield 2-(3-chloro-4-(methylthio)phenyl)acetic acid as a white colored solid (8 g, 85%).

Workup

  1. temperatureslowly heated to 80° C
  2. temperatureto reflux for 12-16 h at the same temperature
  3. customOn completion of the reaction
  4. customthe reaction contents
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  7. filtrationThe precipitate was filtered
  8. customdried

Sources & evidence

ORD record
ord-cd4f331e39d04143824d2a42f952fdd1
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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