Sulfuric Acid → HCID 88219692, compound

HRID 322094

Reaction equation

HRID 322094 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH3:10].[S:11](=O)(=[O:14])([OH:13])[OH:12]>>[OH2:8].[OH2:12].[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([O:8][CH3:9])=[C:6]([S:11]([OH:14])(=[O:13])=[O:12])[CH:7]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 1179151-Bromo-4-methoxy-2-methylbenzene

Product 1

HCID 88219692HCID 88219692, compoundYield 86%

Conditions

Temperature
2.5 °C

Procedure

4-Bromo-3-methylanisole (500 g, 2.5 moles) was cautiously added dropwise over a period of 20-25 minutes to 98% sulfuric acid (1,600 ml) at ambient temperature (exothermic, temperature rise to 42-43° C.) and the reaction stirred for 16 hours. The reaction mixture was cautiously quenched onto cooled (0-5° C.) deionised water (7.5 liter) over a 2 hour period at a rate that maintained the temperature below 20° C. The precipitated product was granulated for 3 hours, filtered and dried to give the crude sulphonic acid (980 g). The crude product was recrystallised from ethyl acetate (2.94 liters, 3 ml/g) to give the subtitle compound (680 g, 86% yield) as a white crystalline solid (mp=131-133° C.)

Workup

  1. customThe reaction mixture was cautiously quenched
  2. temperaturemaintained the temperature below 20° C
  3. waitThe precipitated product was granulated for 3 hours
  4. filtrationfiltered
  5. customdried
  6. customto give the crude sulphonic acid (980 g)
  7. customThe crude product was recrystallised from ethyl acetate (2.94 liters, 3 ml/g)

Sources & evidence

ORD record
ord-442072f131d44a8b8e579264d4dce522
Source dataset
uspto-grants-2001_04
Patent number
US06211223B1

Linked notes

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