Acetic Acid → Styrenesulfonic acid

HRID 484557

Reaction equation

HRID 484557 reaction equation
N[C:2]1[C:3]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:12](O)(=O)[CH3:13].N(OCCCCC)=O.[OH-].[Na+]>CO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH2:12]=[CH:13][C:2]1[C:3]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 69262-Aminobenzenesulfonic acidHCID 10026Pentyl nitriteHCID 14798Sodium Hydroxide

Product 1

HCID 168625Styrenesulfonic acidYield 87.5%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 887MethanolSolvent2×

Procedure

13.0 g of aniline-2-sulphonic acid were suspended in 200 ml of methanol and treated with 20 g of glacial acetic acid. Under a nitrogen atmosphere, 9.5 g of amyl nitrite were added dropwise at a temperature of 0° to 5° C. and the suspension was stirred for 1 hour. A solution of 15 g of NaOH in 100 ml of methanol was then added dropwise at such a rate that the temperature of the mixture did not exceed 20° C. After addition of 0.5 g of bis(dibenzylideneacetone)palladium(0), the mixture was stirred at 20° C. for 3 hours under an ethylene pressure of 20 bar, the solid was then filtered off with suction and the filtrate was evaporated to dryness. 12.1 g (78%) of styrene-2-sulphonic acid, Na salt, were obtained.

Workup

  1. customdid not exceed 20° C
  2. stirringthe mixture was stirred at 20° C. for 3 hours under an ethylene pressure of 20 bar
  3. filtrationthe solid was then filtered off with suction
  4. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-48b29c1265524e6db3ea7f6337d420ad
Source dataset
uspto-grants-1993_07
Patent number
US05231223

Linked notes

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