p-Toluenesulfonic acid → HCID 13592051, compound

HRID 2350983Notes

Reaction equation

HRID 2350983 reaction equation
[SH:1][C:2]1[C:8]([CH3:9])=[C:7]([OH:10])[C:6]([CH3:11])=[C:5]([CH3:12])[C:3]=1[OH:4].[C:13]1(C)[CH:18]=CC(S(O)(=O)=O)=C[CH:14]=1>CC(C)=O>[OH:10][C:7]1[C:6]([CH3:11])=[C:5]([CH3:12])[C:3]2[O:4][C:13]([CH3:18])([CH3:14])[S:1][C:2]=2[C:8]=1[CH3:9]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13089353HCID 13089353, compound

Product 1

HCID 13592051HCID 13592051, compoundYield 7.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4.8 g of 2-mercapto-3,5,6-trimethylhydroquinone, 1 g of p-toluenesulfonic acid, 10 g of molecular sieve 4A and 100 ml of acetone was heated under reflux for 5 hours under a stream of nitrogen. At the end of this time, the acetone was distilled off, and an aqueous solution of sodium bicarbonate was added to the residue. This mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled from the extract. Benzene was added to the resulting residue. Substances which were not soluble in benzene were filtered off, and crystals precipitating from the benzene solution were removed. The portion which was readily soluble in benzene was separated by silica gel column chromatography. The portion eluted with benzene was recrystallized from petroleum ether to yield 0.1 g of the title compound, melting at 62°-64.5° C. Mass spectrum (m/e): 224 (M+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours under a stream of nitrogen
  3. distillationAt the end of this time, the acetone was distilled off
  4. additionan aqueous solution of sodium bicarbonate was added to the residue
  5. extractionThis mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled from the extract
  9. additionBenzene was added to the resulting residue
  10. filtrationwere filtered off
  11. customcrystals precipitating from the benzene solution
  12. customwere removed
  13. customwas separated by silica gel column chromatography
  14. washThe portion eluted with benzene
  15. customwas recrystallized from petroleum ether

Sources & evidence

ORD record
ord-4dcb902ff6824992ad1e32a47d894f48
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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