Hydrochloric Acid → 4-(3,5-Dichloro-4-methylphenyl)-2-methylthio-4-oxobutyric acid

HRID 746270Notes

Reaction equation

HRID 746270 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[O:16])[CH:11]=[CH:12][C:13]([OH:15])=[O:14])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[CH3:17][S-:18].[Na+].Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[O:16])[CH2:11][CH:12]([S:18][CH3:17])[C:13]([OH:15])=[O:14])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 545341534-(3,5-Dichloro-4-methylphenyl)-4-oxobut-2-enoic acid

Product 1

HCID 134203114-(3,5-Dichloro-4-methylphenyl)-2-methylthio-4-oxobutyric acidYield 98.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

2.59 g (0.01 mole) of 4-(3,5-dichloro-4-methylphenyl)-4-oxo-2-butenoic acid, prepared as described in step (b) above, were suspended in 10 ml of water, and then 3.5 g (0.01 mole) of a 20% w/v aqueous solution of sodium methanethiolate were poured into the suspension, whilst water-cooling and stirring. The mixture was then stirred for a further 30 minutes, after which 2 ml of concentrated hydrochloric acid were added dropwise to the mixture, whilst water-cooling, and the resulting crystals were collected by filtration, washed with water and air-dried, to give 3.03 g (yield 98.7%) of the desired 4-(3,5-dichloro-4-methylphenyl)-2-methylthio-4-oxobutyric acid, melting at 158°-160° C.

Workup

  1. temperaturecooling
  2. stirringThe mixture was then stirred for a further 30 minutes
  3. temperaturecooling
  4. filtrationthe resulting crystals were collected by filtration
  5. washwashed with water
  6. customair-dried

Sources & evidence

ORD record
ord-4b4c8996ea3f4a55a65c20203feea39d
Source dataset
uspto-grants-1986_07
Patent number
US04603201

Reaction notes

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