Pyridine → Methyl p-toluenesulfonate

HRID 2388617Notes

Reaction equation

HRID 2388617 reaction equation
O.O.[C:3]1([CH3:13])[CH:8]=[CH:7][C:6]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.N1C=CC=C[CH:15]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.S(OC)(OC)(=O)=O>C(Cl)Cl.C1CCCCC1>[C:3]1([CH3:13])[CH:4]=[CH:5][C:6]([S:9]([O:12][CH3:15])(=[O:10])=[O:11])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6497Dimethyl SulfateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 86626551p-Toluenesulfonic acid dihydrate

Product 1

HCID 6645Methyl p-toluenesulfonate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

To a suspension of p-toluenesulfonic acid dihydrate (10 g, 0.05 mol) in methylene chloride (50 mL), pyridine (5.1 g, 0.06 mol) was added dropwise, and the mixture was reacted at room temperature for 1 hour. After completion of the reaction, the solvent was evaporated to dryness under reduced pressure to obtain a crude product containing pyridinium p-toluenesulfonate salt. To a suspension of this crude product (5 g, 0.020 mol) in cyclohexane (50 mL), dimethyl sulfate (5.0 g, 0.040 mol) was added, and the mixture was reacted at 80° C. for 2 hours. The reaction liquid was condensed under the reduced pressure to obtain the desired product of methyl p-toluenesulfonate. Quantitative analysis by 1H-NMR showed a conversion rate of 90%.

Workup

  1. additionwas added dropwise
  2. customthe mixture was reacted at room temperature for 1 hour
  3. customAfter completion of the reaction
  4. customthe solvent was evaporated to dryness under reduced pressure
  5. customto obtain a crude product
  6. additionwas added
  7. customthe mixture was reacted at 80° C. for 2 hours
  8. customThe reaction liquid
  9. customcondensed under the reduced pressure

Sources & evidence

ORD record
ord-ebd89a0f82964282baec2ee49a4961e2
Source dataset
uspto-grants-2012_09
Patent number
US08269038B2

Reaction notes

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