p-Toluenesulfonic acid → HCID 23291432, compound

HRID 365394Notes

Reaction equation

HRID 365394 reaction equation
[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([O:13][CH3:14])=[O:12])[CH:4](O)[CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:14][O:13][C:11]([C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[S:1][CH2:2][CH:3]=[CH:4]2)=[O:12]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 53944516HCID 53944516, compound

Product 1

HCID 23291432HCID 23291432, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl thiochroman-4-ol-8-carboxylate (0.337 g, 1.50 mmol) was dissolved in toluene (25 ml) and was treated with p-toluenesulphonic acid (0.028 g, 0.15 mmol). The mixture was then heated to reflux with stirring. After 2 h, the reaction mixture was allowed to cool and was washed with sodium hydrogen carbonate solution. The aqueous layer was then extracted with EtOAc (1×), and the combined organic layers were dried (Na2SO4) and evaporated under reduced pressure to give a pale yellow oil which was purified by silica-gel chromatography (pentane: Et2O 2:1 as eluant) to give the title compound (D2b) as a pale yellow oil (0.270 g, 87%)

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux
  3. temperatureto cool
  4. washwas washed with sodium hydrogen carbonate solution
  5. extractionThe aqueous layer was then extracted with EtOAc (1×)
  6. dry with materialthe combined organic layers were dried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customto give a pale yellow oil which
  9. customwas purified by silica-gel chromatography (pentane: Et2O 2:1 as eluant)

Sources & evidence

ORD record
ord-94768fded6524726a191294fe9c28b96
Source dataset
uspto-grants-2000_10
Patent number
US06127379

Reaction notes

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