Methanol → Benzoic acid, 3-(chlorosulfonyl)-, methyl ester

HRID 554248Notes

Reaction equation

HRID 554248 reaction equation
[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8](Cl)=[O:9])(=[O:4])=[O:3].N1C=CC=CC=1.[CH3:20][OH:21]>ClCCl>[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:21][CH3:20])=[O:9])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 1049PyridineHCID 77671Benzoyl chloride, 3-(chlorosulfonyl)-

Product 1

HCID 113339Benzoic acid, 3-(chlorosulfonyl)-, methyl esterYield 92.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution (20 mL) of 3-(chlorosulfonyl)benzoyl chloride (2.4 g) in dichloromethane was cooled to 0° C., and pyridine (791 mg) and methanol (320 mg) were added. The reaction mixture was stirred at room temperature for 2 hr, and the solvent was evaporated under reduced pressure. The residue was filtrated, washed with a mixed solvent of ethyl acetate and isopropyl ether, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1) to give the title compound as a colorless oil (yield 2.17 g, 92%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. filtrationThe residue was filtrated
  3. washwashed with a mixed solvent of ethyl acetate and isopropyl ether
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9:1→4:1)

Sources & evidence

ORD record
ord-6a069e1cf54f447093f21975127268d3
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

Loading…