Methanesulfonyl chloride → Methyl 2-[(methanesulfonyl)oxy]-4-nitrobenzoate

HRID 280833Notes

Reaction equation

HRID 280833 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:15][S:16]([O:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])(=[O:18])=[O:17]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 139539Salicylic acid, 4-nitro-, methyl ester

Product 1

HCID 23320160Methyl 2-[(methanesulfonyl)oxy]-4-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
50 °C

Procedure

Methyl 2-hydroxy-4-nitrobenzoate (19.7 g) was dissolved in 100 ml of chloroform and triethylamine (15 ml). The solution was kept at a temperature below 15° C., and methanesulfonylchloride (8.6 ml) was added dropwise. The solution was maintained at 50° C. for 1 hr, whereupon it was poured onto ice-hydrochloric acid and extracted with a total of 600 ml chloroform. The solution was dried with magnesium sulfate, treated with active carbon and evaporated. The product was recrystallized from methanol. Yield: 20 g.

Workup

  1. additionwas added dropwise
  2. additionwas poured onto ice-hydrochloric acid
  3. extractionextracted with a total of 600 ml chloroform
  4. dry with materialThe solution was dried with magnesium sulfate
  5. additiontreated with active carbon
  6. customevaporated
  7. customThe product was recrystallized from methanol

Sources & evidence

ORD record
ord-e999d4d5001244278c3eb477e6871205
Source dataset
uspto-grants-1986_05
Patent number
US04591584

Reaction notes

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