Hydroxybenzenesulfonic acid → Benzenesulfonic Acid

HRID 1837007Notes

Reaction equation

HRID 1837007 reaction equation
O.[C:2]1([S:8]([OH:11])(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[C:2]1([S:8]([OH:11])(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 15619088Hydroxybenzenesulfonic acid

Product 1

HCID 7371Benzenesulfonic AcidYield 291.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Bezenesulfonic acid monohydrate (1.06 g, 6 mmol) was dried by azeotroping off the water of a benzene solution (twice) and adding the dried acid solution to a solution of example 415 (2.81 g, 6 mmol) in toluene (40 ml). The solvents were removed in vacuo (twice) and the resulting residue recrystallized twice from toluene and dried under high vacuum overnight give 2.77 g of benzenesulfonic acid salt as a white solid. mp 157-159° C. [α]D25=16.9° (CH3OH, c=0.23 g/dL). Anal. Calcd for C34H42N3O5FS: C, 65.47; H 6.80; N, 6.75; S, 5.14. Found: C, 65.48; H, 6.80; N, 6.70; S, 5.35.

Workup

  1. customby azeotroping off the water of a benzene solution (twice) and
  2. customThe solvents were removed in vacuo (twice) and the resulting residue
  3. customrecrystallized twice from toluene
  4. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-f71c001126604bf1ad17cc1d00a99615
Source dataset
uspto-grants-2004_08
Patent number
US06780857B2

Reaction notes

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