Hydrochloric Acid → Benzenesulfonic acid, 2-nitro-, methyl ester

HRID 571577Notes

Reaction equation

HRID 571577 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[CH3:14][OH:15].C[O-].[Na+].Cl>O>[CH3:14][O:15][S:10]([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:11])=[O:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 155402-Nitrobenzenesulfonyl chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 169151Benzenesulfonic acid, 2-nitro-, methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

856 g of 2-nitrobenzenesulfonyl chloride and 7 L of methanol are placed in a reaction container having a stirrer, a thermometer, and a nitrogen introducing pipe attached thereto, and a mixed solution of 745 g of 28% sodium methylate and 600 mL of methanol is dropped at a temperature of not more than 10° C. over 45 minutes. Subsequently, the solution is stirred for 50 minutes while the temperature is kept at 10° C. 1.6 kg of 0.1 mol/L hydrochloric acid is added to the reaction mixture to make the reaction solution acidic, and 3 L of water is further added to precipitate crystals. The crystals are filtered out, and washed with 2 L of water. Then, the crystals are dried under reduced pressure at 30° C. for 10 hours to obtain 702 g of 2-nitrobenzenesulfonic acid methyl ester.

Workup

  1. customis kept at 10° C
  2. customto precipitate crystals
  3. filtrationThe crystals are filtered out
  4. washwashed with 2 L of water
  5. customThen, the crystals are dried under reduced pressure at 30° C. for 10 hours

Sources & evidence

ORD record
ord-e26da3bb7196482584e7adbf82d8fb86
Source dataset
uspto-grants-2015_05
Patent number
US09029056B2

Reaction notes

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