p-Toluenesulfonic acid monohydrate → HCID 18615089, compound

HRID 565450

Reaction equation

HRID 565450 reaction equation
[C:1]([C:4]1[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH2:15].[C:16]1([CH3:26])C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(O)CO>[CH2:16]1[O:15][C:1]([C:4]2[CH:14]=[CH:13][C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][CH:5]=2)([CH3:2])[O:3][CH2:26]1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 600911Ethyl 4-acetylbenzoate

Product 1

HCID 18615089HCID 18615089, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 1140TolueneSolvent

Procedure

ethyl 4-acetyl-benzoate (9.61 g, a product of the firm Wako Pure Chemical Ind.) was dissolved in toluene (200 ml) under an argon atmosphere whereto ethylene glycol (20 ml) and p-toluenesulfonic acid hydrate (200 mg) were added, whereupon the mixture was refluxed with heating for 24 hours while dehydrating on a Dean-Stark apparatus. After cooling down to room temerature, the toluene layer was washed with water (100 ml×twice) and with saturated aqueous sodium chloride solution (100 ml) succeedingly, followed by drying and concentrating to dryness under reduced pressure, whereby the above-identified compound was obtained (12.76 g).

Workup

  1. additionwere added, whereupon the mixture
  2. temperaturewas refluxed
  3. temperaturewith heating for 24 hours
  4. temperatureAfter cooling down to room temerature
  5. washthe toluene layer was washed with water (100 ml×twice) and with saturated aqueous sodium chloride solution (100 ml) succeedingly
  6. customby drying
  7. concentrationconcentrating to dryness under reduced pressure, whereby the above-identified compound
  8. customwas obtained (12.76 g)

Sources & evidence

ORD record
ord-4162c50c57c448d4880a91b9ace26986
Source dataset
uspto-grants-2001_01
Patent number
US06172099B2

Linked notes

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