Triethylamine → HCID 18977988, compound

HRID 1491559Notes

Reaction equation

HRID 1491559 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 one-half hour and left to stand overnight. The mixture was washed with hydrochloric acid (2M), saturated aqueous sodium bicarbonate solution, water, dried (Na2SO4) 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. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-de27192d9e0a48389d5624ce0ec84507
Source dataset
uspto-grants-1994_12
Patent number
US05371063

Reaction notes

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