4-Hydroxybenzenesulfonicacid,disodiumsalt → Sodium 4-[(2-chlorononanoyl)oxy]benzenesulfonate

HRID 1153701Notes

Reaction equation

HRID 1153701 reaction equation
[CH:1]1[C:6]([O-:7])=[CH:5][CH:4]=[C:3]([S:8]([O-:11])(=[O:10])=[O:9])[CH:2]=1.[Na+:12].[Na+].[Cl:14][CH:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:16](Cl)=[O:17]>>[Cl:14][CH:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:16]([O:7][C:6]1[CH:1]=[CH:2][C:3]([S:8]([O-:11])(=[O:9])=[O:10])=[CH:4][CH:5]=1)=[O:17].[Na+:12]

Participants

3

Reactant 2

HCID 133190634-Hydroxybenzenesulfonicacid,disodiumsaltHCID 202674982-Chlorononanoyl chloride

Product 1

HCID 23674303Sodium 4-[(2-chlorononanoyl)oxy]benzenesulfonateYield 68%

Procedure

Anhydrous disodium p-phenolsulfonate (28.5 g; 0.130 mole) and 30.3 g (0.1436 mole) of 2-chlorononanoyl chloride were combined in a 500 ml round-bottomed flask. The flask was then immersed in an oil bath which had been preheated to 110° C. Within five minutes an exothermic reaction occurred which caused the entire mixture to congeal. After cooling, the mixture was triturated three times with 150-200 ml portions of ether and the product was vacuum dried. Elemental and nmr analyses of the resulting tan powder, 46.2 g, indicated that it was composed of 11.5% NaCl, 17.7% disodium p-phenolsulfonate, and 70.8% of sodium p-(2-chlorononanoyloxy)benzene sulfonate. This represents a 68% yield of the desired product.

Workup

  1. customThe flask was then immersed in an oil bath
  2. customhad been preheated to 110° C
  3. customWithin five minutes an exothermic reaction
  4. temperatureAfter cooling
  5. customthe mixture was triturated three times with 150-200 ml portions of ether
  6. customdried

Sources & evidence

ORD record
ord-5d27ed97bc4b4f9d8082932680965dc6
Source dataset
uspto-grants-1984_12
Patent number
US04486327

Reaction notes

Loading…