Methyl p-toluenesulfonate → p-Toluenesulfonic acid

HRID 1665829Notes

Reaction equation

HRID 1665829 reaction equation
C[O:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4]>C(OCC)(=O)C>[CH3:12][C:9]1[CH:10]=[CH:11][C:6]([S:3]([OH:5])(=[O:4])=[O:2])=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 6645Methyl p-toluenesulfonate

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

When the reaction ended, the mixture was allowed to cool and was left to stand overnight. The crystals that precipitated were filtered out, washed with dimethyl formamide, and dried under reduced pressure, yielding 3.0 g of intermediate B. To 2.0 g of intermediate B was then added 20 mL of p-toluenesulfonic acid methyl ester, and the mixture was stirred with heating for 6 hours at 120° C. The mixture was allowed to cool, after which 30 mL of ethyl acetate was added, and stirring was conducted for 30 minutes. The precipitating crystals were filtered out and dried, yielding 2.75 g of p-toluenesulfonate of V-1.

Workup

  1. temperatureto cool
  2. waitwas left
  3. customThe crystals that precipitated
  4. filtrationwere filtered out
  5. washwashed with dimethyl formamide
  6. customdried under reduced pressure
  7. customyielding 3.0 g of intermediate B
  8. temperatureto cool
  9. stirringstirring
  10. waitwas conducted for 30 minutes
  11. filtrationThe precipitating crystals were filtered out
  12. customdried

Sources & evidence

ORD record
ord-db6a7bdd4bcc4061b50b8150661bbffa
Source dataset
uspto-grants-2011_10
Patent number
US08039630B2

Reaction notes

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