Methanesulfonyl chloride → Methyl 4-methyl-3-[(methylsulfonyl)oxy]benzoate

HRID 507990Notes

Reaction equation

HRID 507990 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[CH3:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[O:1][S:14]([CH3:13])(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 354091Methyl 3-hydroxy-4-methylbenzoate

Product 1

HCID 23157501Methyl 4-methyl-3-[(methylsulfonyl)oxy]benzoateYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-hydroxy-4-methylbenzoate (3.0 g, 18.1 mmol) in pyridine (20 mL) was added methanesulfonyl chloride (2.80 mL, 36.1 mmol) under stirring at 0° C., and the mixture was stirred at room temperature for 3 hr. The solvent was evaporated under reduced pressure, and the residue was partitioned between ethyl acetate and 1 N hydrochloric acid. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1) to give the title compound (4.11 g, yield 93%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and 1 N hydrochloric acid
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-35d3c1d32d5246819302e6b49416b1ef
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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