Pyridine → 1-Butanesulfonic acid, methyl ester

HRID 2388616Notes

Reaction equation

HRID 2388616 reaction equation
[CH2:1]([S:5]([OH:8])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4].N1C=CC=C[CH:10]=1.C(S([O-])(=O)=O)CCC.[NH+]1C=CC=CC=1.S(OC)(OC)(=O)=O>C(Cl)Cl.C1CCCCC1>[CH2:1]([S:5]([O:8][CH3:10])(=[O:7])=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6497Dimethyl SulfateHCID 499351-Butanesulfonic acidHCID 19795495Pyridin-1-ium butane-1-sulfonate

Product 1

HCID 1427601-Butanesulfonic acid, methyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

After 1-butanesulfonic acid (10 g, 0.072 mol) was dissolved in methylene chloride (50 mL), pyridine (11 g, 0.14 mol) was added dropwise thereto, and the mixture was reacted at room temperature for 2 hours. After completion of the reaction, the solvent was evaporated under the reduced pressure to dryness to obtain a crude product containing pyridinium 1-butanesulfonate salt. To a suspension of this crude product (5 g, 0.023 mol) in cyclohexane (50 mL), dimethyl sulfate (15 g, 0.12 mol) was added, and the mixture was reacted at 80° C. for 2 hours. The resultant reaction liquid was condensed under the reduced pressure to obtain the desired product of methyl 1-butanesulfonate. Quantitative analysis by 1H-NMR showed a conversion rate of 77%.

Workup

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

Sources & evidence

ORD record
ord-7b313362ca6d4b85b29149b9acfa77e1
Source dataset
uspto-grants-2012_09
Patent number
US08269038B2

Reaction notes

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