p-Toluenesulfonic acid → 116833-86-4

HRID 1905545Notes

Reaction equation

HRID 1905545 reaction equation
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[CH:18]([C:22]([OH:24])=[O:23])[CH2:17][CH2:16]2>CO>[OH:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[CH:18]([C:22]([O:24][CH3:1])=[O:23])[CH2:17][CH2:16]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 20035831116833-85-3

Product 1

HCID 20035828116833-86-4Yield 10,949.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

In a 20-liter reactor with a mechanical stirrer, 1.6 kg of 2,3-dihydro-5-hydroxy-1H-inden-1-carboxylic acid were dissolved with 7.2 l of absolute methanol, 9 g of p-toluenesulphonic acid were added and then refluxed under stirring in oil bath heated at 90° C. for 24 hours. The mixture was allowed to cool, the excess of methanol was evaporated at vacuum, the residue was diluted with 1.5 l of water, 1.5 l of sodium bicarbonate saturated solution and 5 l of toluene and then stirred for 30 minutes. The insoluble material was filtered, washed twice with 1 l of toluene; the aqueous phase was extracted with 2 l of toluene, and the organic phases were filtered using a filter paper and washed with water. The toluene phase was concentrated at vacuum to give a blackish, viscous liquid residue weighing 1.391 kg (88%), which was distilled at vacuum to give 1.1 kg (70%) of colourless liquid at 124°-137° C./0.03-0.025 tors, nD20 =1.5533, IR and 1H-NMR spectra were consistent with structure.

Workup

  1. additionwere added
  2. temperaturerefluxed
  3. temperatureto cool
  4. customthe excess of methanol was evaporated at vacuum
  5. additionthe residue was diluted with 1.5 l of water, 1.5 l of sodium bicarbonate saturated solution and 5 l of toluene
  6. stirringstirred for 30 minutes
  7. filtrationThe insoluble material was filtered
  8. washwashed twice with 1 l of toluene
  9. extractionthe aqueous phase was extracted with 2 l of toluene
  10. filtrationthe organic phases were filtered
  11. washwashed with water
  12. concentrationThe toluene phase was concentrated at vacuum
  13. customto give a blackish, viscous liquid residue
  14. distillationwas distilled at vacuum

Sources & evidence

ORD record
ord-44a6ec252716417f8270b5de7755230a
Source dataset
uspto-grants-1989_06
Patent number
US04843165

Reaction notes

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