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

HRID 72078Notes

Reaction equation

HRID 72078 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

Conditions

Temperature
10 °C

Procedure

A reaction vessel equipped with a stirrer, a thermometer, and a nitrogen inlet tube was charged with 856 g of 2-nitrobenzenesulfonyl chloride and 7 L of methanol, and then a mixed solution of 745 g of 28% sodium methylate and 600 ml of methanol was dropped for 45 minutes at a temperature of 10° C. or less. The mixture was then stirred for 50 minutes while maintaining the temperature at 10° C. The reaction mixture was acidified by adding 1.6 kg of 0.1 mol/l hydrochloric acid, and then adding 3 L of water, whereby crystals deposited. The crystals were filtered, washed with 2 L of water, and then dried under reduced pressure for 10 hours at 30° C. to obtain 702 g of 2-nitrobenzene sulfonic acid methyl ester.

Workup

  1. customA reaction vessel equipped with a stirrer
  2. filtrationThe crystals were filtered
  3. washwashed with 2 L of water
  4. customdried under reduced pressure for 10 hours at 30° C.

Sources & evidence

ORD record
ord-aa19dad4ff1b45429c6f6f1c3ec4c5ec
Source dataset
uspto-grants-2014_09
Patent number
US08828633B2

Reaction notes

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