Toluene → HCID 18319101, compound

HRID 1383950Notes

Reaction equation

HRID 1383950 reaction equation
[OH:1][CH2:2][CH2:3][S:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:10][CH:9]=1.C1(C)C=CC(S(O)(=O)=[O:26])=CC=1.[C:30]1([CH3:36])C=CC=CC=1>C(O)(=O)C>[C:30]([O:1][CH2:2][CH2:3][S:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:13]=1)(=[O:26])[CH3:36]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 18319089HCID 18319089, compound

Product 1

HCID 18319101HCID 18319101, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-[4-[2-(2-hydroxyethylthio)ethoxy]phenyl]propanoic acid, (35.67 g, 0.13 mol) in a mixture of toluene (500 ml) and acetic acid (500 ml) was treated with p-toluenesulfonic acid (1.2 g) and then heated under reflux using a Dean-Stark apparatus for 2 h. The cooled mixture was concentrated in vacuo and the residue was diluted with ethyl acetate, washed with water and dried (magnesium sulfate). Evaporation of the solvent under vacuum gave a solid which was crystallized from hexane to give 36.13 g (88%) of title material as a white solid: mp 48-49° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. customfor 2 h
  4. concentrationThe cooled mixture was concentrated in vacuo
  5. additionthe residue was diluted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried (magnesium sulfate)
  8. customEvaporation of the solvent under vacuum
  9. customgave a solid which
  10. customwas crystallized from hexane

Sources & evidence

ORD record
ord-a905dffaeb5248b9a316f88787dc7ccc
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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