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

HRID 1628148Notes

Reaction equation

HRID 1628148 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 ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Hydroxy-benzoic acid methyl ester (3.19 g, 21 mmol) was dissolved together with pyridine (1.97 g, 25 mmol) in dry THF (20 mL) and after cooling down to 0° C., methanesulfonyl chloride (2.29 g, 20 mmol) was added dropwise. The ice bath was removed and mixture was stirred at r.t. for 5 h. After diluting with DCM and extraction with water and aq. HCl (2N), the organic layer was dried (MgSO4) and evaporated to afford the crude but highly pure product as a solid which was used in the next step without further purification (4.38 g, 95.1%). 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. customThe ice bath was removed
  2. additionAfter diluting with DCM and extraction with water and aq. HCl (2N)
  3. dry with materialthe organic layer was dried (MgSO4)
  4. customevaporated
  5. customto afford the crude but highly pure product as a solid which
  6. customwas used in the next step without further purification (4.38 g, 95.1%)

Sources & evidence

ORD record
ord-473bd525df774a53bbd61e4958f21761
Source dataset
uspto-grants-2014_07
Patent number
US08785681B2

Reaction notes

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