Trimethyl orthoacetate → Methyl 4,5-bismethanesulfonyl-2-methylbenzoate

HRID 49648Notes

Reaction equation

HRID 49648 reaction equation
Cl[C:2]1[C:10]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:9][C:5](C(O)=O)=[C:4](C)[CH:3]=1.[C:16](OC)([O:20][CH3:21])([O:18]C)[CH3:17]>CN1C(=O)CCC1>[CH3:14][S:11]([C:10]1[C:9]([S:11]([CH3:10])(=[O:13])=[O:12])=[CH:5][C:17]([C:16]([O:20][CH3:21])=[O:18])=[C:3]([CH3:4])[CH:2]=1)(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 108244784-chloro-2-methyl-5-(methylsulfonyl)Benzoic acid

Product 1

HCID 11738318Methyl 4,5-bismethanesulfonyl-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 100.0 g of 4-chloro-5-methanesulfonyl-2-methylbenzoic acid and 68.1 g of trimethyl orthoacetate in 322 ml of NMP was refluxed until the acid had reacted completely. After the excess orthoester had been distilled off, 96.5 g of sodium methanesulfinate were added, and the mixture was stirred at 90° C. for 18 h. Conventional work-up gave methyl 4,5-bis-methanesulfonyl-2-methylbenzoate.

Workup

  1. customhad reacted completely
  2. distillationAfter the excess orthoester had been distilled off
  3. addition96.5 g of sodium methanesulfinate were added

Sources & evidence

ORD record
ord-7728b859049a420483ed9f879c6ba36d
Source dataset
uspto-grants-2004_03
Patent number
US06706921B2

Reaction notes

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