Pyridine → Benzoic acid, 4-[(methylsulfonyl)oxy]-, methyl ester

HRID 709444Notes

Reaction equation

HRID 709444 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.N1C=CC=CC=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C1COCC1>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][S:19]([CH3:18])(=[O:21])=[O:20])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7456MethylparabenHCID 31297Methanesulfonyl chloride

Product 1

HCID 10466383Benzoic acid, 4-[(methylsulfonyl)oxy]-, methyl esterYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Hydroxybenzoic acid methylester (2.29 g, 20 mmol) was dissolved together with pyridine (2.02 mL, 25 mmol) in anhydrous THF (20 mL) and after cooling down to 0° C., methanesulfonyl chloride (2.16 mL, 21 mmol) was added dropwise. After complete addition the ice bath was removed and the mixture was stirred at room temperature for 5 h. The slurry was diluted with DCM and extracted with H2O and aq. HCl (2N). The separated organic layer was finally dried (MgSO4) and evaporated to afford the crude product as an oil (4.38 g, 95%). 1H NMR (400 MHz, CDCl3): δ 8.07-8.09 (d, 2H), 7.32-7.34 (d, 2H), 3.90 (s, 3H), 3.16 (s, 3H).

Workup

  1. customwas removed
  2. additionThe slurry was diluted with DCM
  3. extractionextracted with H2O and aq. HCl (2N)
  4. dry with materialThe separated organic layer was finally dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-fc636999ff8a4c9eb5f547d56b36c282
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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