Hydrochloric Acid → HCID 54736792, compound

HRID 1579585Notes

Reaction equation

HRID 1579585 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[SH:10].Cl[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1.Cl>N1C=CC=CC=1>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[S:10][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][S:10][C:3]2[C:4](=[O:9])[O:5][C:6]([CH3:8])=[CH:7][C:2]=2[OH:1])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12171alpha,alpha'-Dichloro-p-xyleneHCID 547312374-Hydroxy-3-mercapto-6-methyl-2-pyrone

Product 1

HCID 54736792HCID 54736792, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 15.8 g. (0.100 mole) of 4-hydroxy-3-mercapto-6-methyl-2-pyrone in 100 ml. of pyridine was added 8.75 g. (0.0500 mole) of α,α'-dichloro-p-xylene in one portion at room temperature. The reaction mixture was allowed to stand at room temperature for 15 hours and then was poured into a mixture of ice and 200 ml. of concentrated hydrochloric acid. The mixture was extracted with methylene chloride, leaving the methylene chloride-insoluble, white solid product behind. This was collected on a filter and found to weigh 5.3 g., m.p. 224°C. (dec.). The extract was dried over anhydrous sodium sulfate, and the methylene chloride was removed by evaporation in vacuo. The remaining 4.1 g. of light yellow solid residue was triturated with benzene containing a little ethanol, leaving 1.7 g. more product as an insoluble white solid, m.p. 228°-229°C. (dec.). Recrystallization of the combined product fractions from nitromethane gave the pure α,α'-bis(4-hydroxy-6-methyl-2-oxo-3-pyranylthio)-p-xylene as very pale yellow crystals, m.p. 234°C. (dec.).

Workup

  1. customat room temperature
  2. additionwas poured into a mixture of ice and 200 ml
  3. extractionThe mixture was extracted with methylene chloride
  4. customleaving the methylene chloride-insoluble, white solid product behind
  5. customThis was collected on
  6. filtrationa filter
  7. dry with materialThe extract was dried over anhydrous sodium sulfate
  8. customthe methylene chloride was removed by evaporation in vacuo
  9. customof light yellow solid residue was triturated with benzene containing a little ethanol
  10. customleaving 1.7 g
  11. customRecrystallization of the combined product fractions from nitromethane

Sources & evidence

ORD record
ord-43b8bfb2db65440582cf3b7362c913d7
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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