Sodium 4-hydroxybenzenesulfonate → HCID 22645035, compound

HRID 2084869Notes

Reaction equation

HRID 2084869 reaction equation
[Na+].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.Br[CH2:14][C:15]#[C:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1>C(O)(C)C.[OH-].[Na+]>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]#[C:15][CH2:14][O:2][C:3]2[CH:8]=[CH:7][C:6]([S:9]([OH:12])(=[O:10])=[O:11])=[CH:5][CH:4]=2)=[CH:18][CH:19]=1

Participants

5

Reactant 2

HCID 4379756Sodium 4-hydroxybenzenesulfonateHCID 10513607173019-82-4

Product 1

HCID 22645035HCID 22645035, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-hydroxybenzenesulfonic acid sodium salt (2.81 g, 12.11 mmol) in 50 mL of isopropyl alcohol, 11.8 mL 2N NaOH and 5.56 g (24.2 mmol, 2 eq) of 1-(3-bromo-prop-1-ynyl)-4-chloro-benzene was added. The solution was heated to 70° C. overnight. The reaction was cooled, concentrated in vacuo, filtered and air dried to afford 2.8 g (67%) of 4-[3-(4-chloro-phenyl)-prop-2-ynyloxy]-benzenesulfonic acid, sodium salt. Electrospray Mass Spec 321.3 (M−H)−.

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. filtrationfiltered
  4. customair dried

Sources & evidence

ORD record
ord-9eb7afabdca344be9bb0462ffb71e3e8
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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