Methanol → HCID 1898172, compound

HRID 1720846Notes

Reaction equation

HRID 1720846 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([S:16](Cl)(=[O:18])=[O:17])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])C=1O)([CH3:4])([CH3:3])[CH3:2].[CH3:20][OH:21].N1C=CC=C[CH:23]=1.[OH2:28]>>[C:12]([C:9]1[CH:8]=[C:7]([S:16]([O:18][CH3:23])(=[O:17])=[O:28])[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:20]=1[OH:21])([CH3:13])([CH3:14])[CH3:15]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 1049PyridineHCID 153329423,5-Di-tert-butyl-4-hydroxybenzene-1-sulfonyl chloride

Product 1

HCID 1898172HCID 1898172, compoundYield 78.7%

Procedure

To a mixture of 10.0 g (32.4 mmol) of 3,5-di-tertiary-butyl-4-hydroxybenzenesulfonyl chloride, prepared as described above, and 50 ml of anhydrous methanol was added 2.56 g (32.4 mmol) of pyridine. An exothermic reaction ensued resulting in a solution. The solution was stirred at room temperature for 30 minutes and poured into water. A white solid precipitate formed which was collected and dissolved in methylene chloride. The solution was washed with water, dried over magnesium sulfate and concentrated. The solid residue was recrystallized from heptane to give 7.66 g of, as a white crystalline product, methyl 3,5-di-tertiary-butyl-4-hydroxybenzenesulfonate (78.7% of theory); mp=116.5°-18° C.

Workup

  1. customprepared
  2. customAn exothermic reaction
  3. customensued resulting in a solution
  4. customA white solid precipitate formed which
  5. customwas collected
  6. dissolutiondissolved in methylene chloride
  7. washThe solution was washed with water
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe solid residue was recrystallized from heptane

Sources & evidence

ORD record
ord-efad250cd4114b6a80f044a2f5a8025f
Source dataset
uspto-grants-1996_04
Patent number
US05508140

Reaction notes

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