Water → 1-[5-(4-Chlorophenyl)-4-hydroxythiophen-3-yl]ethan-1-one

HRID 1967593Notes

Reaction equation

HRID 1967593 reaction equation
C(Cl)(Cl)Cl.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[C:16]([OH:17])=[C:15]([C:18]([CH3:20])=[O:19])[CH2:14][S:13]2)=[CH:8][CH:7]=1.S(Cl)(Cl)(=O)=O.O>C(O)(C)C>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[S:13][CH:14]=[C:15]([C:18]([CH3:20])=[O:19])[C:16]=2[OH:17])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6212Chloroform2×HCID 24648Sulfuryl chlorideHCID 442070432-(4-Chlorophenyl)-3-hydroxy-4-methylcarbonyl-2,5-dihydrothiophene

Product 1

HCID 442072911-[5-(4-Chlorophenyl)-4-hydroxythiophen-3-yl]ethan-1-oneYield 77%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
-35 °C

Procedure

A chloroform (100 mL) solution of 2-(4-chlorophenyl)-3-hydroxy-4-methylcarbonyl-2,5-dihydrothiophene (10.00 g, 37.29 mmol, purity: 95%) was cooled to −40° C., and to this solution, a chloroform (150 mL) solution of sulfuryl chloride (3.6 mL, 1.2 equivalent amounts) was dropwise added over a period of 50 minutes, followed by stirring at −35° C. for 40 minutes. The temperature of the solution was raised to −3° C., and water (20 mL) was dropwise added, followed by liquid separation. The obtained chloroform solution was sequentially washed with water, a saturated salt solution, a saturated sodium hydrogencarbonate aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off to obtain a crude product. The obtained crude product was suspended in isopropyl alcohol (100 mL) at room temperature, followed by stirring at 0° C. for 15 minutes. The formed crystals were subjected to filtration to give the desired product as a yellow solid (7.26 g, yield: 77%).

Workup

  1. temperatureThe temperature of the solution was raised to −3° C.
  2. customfollowed by liquid separation
  3. washThe obtained chloroform solution was sequentially washed with water
  4. dry with materiala saturated salt solution, a saturated sodium hydrogencarbonate aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated salt solution, and dried over anhydrous magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. distillationthe solvent was distilled off
  7. customto obtain a crude product
  8. customThe obtained crude product
  9. stirringby stirring at 0° C. for 15 minutes
  10. filtrationThe formed crystals were subjected to filtration

Sources & evidence

ORD record
ord-8b68c91106f143d6a4659f184005456c
Source dataset
uspto-grants-2013_04
Patent number
US08420849B2

Reaction notes

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