Hydrochloric Acid → 4-(3,5-Dichloro-4-methylphenyl)-2-ethoxythiocarbonylthio-4-oxobutenoic acid

HRID 746281Notes

Reaction equation

HRID 746281 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].[C:17](=[S:22])([O:19][CH2:20][CH3:21])[S-:18].[K+].Cl>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[O:16])[CH:11]=[C:12]([S:22][C:17]([O:19][CH2:20][CH3:21])=[S:18])[C:13]([OH:15])=[O:14])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2735045Potassium ethylxanthateHCID 545341534-(3,5-Dichloro-4-methylphenyl)-4-oxobut-2-enoic acid

Product 1

HCID 541542144-(3,5-Dichloro-4-methylphenyl)-2-ethoxythiocarbonylthio-4-oxobutenoic acidYield 94.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 2.59 g (0.01 mole) of 4-(3,5-dichloro-4-methylphenyl)-4-oxo-2-butenoic acid and 1.60 g (0.01 mole) of potassium O-ethyl dithiocarbonate in 40 ml of water was stirred at room temperature for 3 hours. At the end of this time, the mixture was ice-cooled, acidified by the addition of concentrated hydrochloric acid and then extracted with diethyl ether. The extract was subjected to column chromatography through silica gel, to give 3.60 g (yield 94.5%) of the desired 4-(3,5-dichloro-4-methylphenyl)-2-ethoxythiocarbonylthio-4-oxobutenoic acid, melting at 126°-128° C.

Workup

  1. temperaturecooled
  2. extractionextracted with diethyl ether

Sources & evidence

ORD record
ord-cd72222ed2ed4ef58a1b0ce72820fdcb
Source dataset
uspto-grants-1986_07
Patent number
US04603201

Reaction notes

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