Triethylamine → HCID 18977988, compound

HRID 2393012Notes

Reaction equation

HRID 2393012 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([OH:17])[C:10](=[CH:15][CH:16]=1)[C:11]([O:13][CH3:14])=[O:12].C(N(CC)CC)C>ClCCl>[Cl:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([O:17][S:2]([CH3:1])(=[O:4])=[O:3])[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 327085Methyl 4-chloro-2-hydroxybenzoate

Product 1

HCID 18977988HCID 18977988, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methane sulphonyl chloride (7.0 g) was added to a stirred, cooled mixture of methyl 4-chlorosalicylate (10.0 g) and triethylamine (8.0 g) in dichloromethane while maintaining the temperature at 0° C. The mixture was then stirred at room temperature for half and hour and left to stand overnight. The mixture was washed with hydrochloric acid (2M) saturated aqueous sodium bicarbonate solution, water, dried (Na2 SO4) and filtered. The filtrate was evaporated to dryness to give methyl 4-chloro-2-(methylsulphonyloxy)benzoate (11.7 g) as an orange solid m.p. 82.5°-84.5° C.

Workup

  1. temperaturecooled
  2. waitleft
  3. washThe mixture was washed with hydrochloric acid (2M) saturated aqueous sodium bicarbonate solution, water
  4. customdried (Na2 SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-99686320be5c42749643408424281098
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Reaction notes

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