p-Toluenesulfonic acid → HCID 13066700, compound

HRID 1163979Notes

Reaction equation

HRID 1163979 reaction equation
O[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([OH:19])=[O:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[OH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][C:7]1[C:2]2[O:19][C:17](=[O:18])[CH2:16][C:3]=2[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13066674HCID 13066674, compound

Product 1

HCID 13066700HCID 13066700, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-[2-hydroxy-3-(2-hydroxyphenoxy)phenyl]acetic acid (9.4 g) and p-toluene sulfonic acid (0.2 g) in benzene (100 ml) was refluxed under heating for 3 hrs. Benzene (20 ml) was distilled off from the reaction mixture, and benzene (20 ml) was newly added and refluxed again under heating for 3 hrs. The reaction mixture was washed with water, aqueous sodium bicarbonate and saline successively, dried over magnesium sulfate and then evaporated. The precipitates were recrystallized from ethanol (10 ml) to give 7-(2-hydroxyphenoxy)-2,3-dihydrobenzofuran-2-one (6.2 g). mp 150°-152.5° C.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating for 3 hrs
  3. distillationBenzene (20 ml) was distilled off from the reaction mixture, and benzene (20 ml)
  4. additionwas newly added
  5. temperaturerefluxed again
  6. temperatureunder heating for 3 hrs
  7. washThe reaction mixture was washed with water, aqueous sodium bicarbonate and saline successively
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customThe precipitates were recrystallized from ethanol (10 ml)

Sources & evidence

ORD record
ord-0dd6d363b99f4860a2f78634fbc11da2
Source dataset
uspto-grants-1983_01
Patent number
US04367238

Reaction notes

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