Sodium Hydroxide → 4-But-2-ynyloxy-benzenesulfonic acid sodium salt

HRID 278330Notes

Reaction equation

HRID 278330 reaction equation
[Na+:1].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-].[Na+].Br[CH2:16][C:17]#[C:18][CH3:19]>C(O)(C)C>[Na+:1].[CH2:16]([O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:12])(=[O:10])=[O:11])=[CH:5][CH:4]=1)[C:17]#[C:18][CH3:19]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27568621-Bromo-2-butyneHCID 4379756Sodium 4-hydroxybenzenesulfonate

Product 1

HCID 237040564-But-2-ynyloxy-benzenesulfonic acid sodium saltYield 81%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4-hydroxybenzenesulfonate sodium salt (52.35 g, 0.225) in 1 L of isopropanol and 225 mL of a 1.0N solution of sodium hydroxide was added 59.96 g (0.45 mol) of 1 bromo-2-butyne. The resulting mixture was heated to 70° for 15 h and then the isopropanol was removed by evaporation in vacuo. The resulting white precipitate was collected by filtration, washed with isopropanol and ether and dried in vacuo to give 45.08 g (81%) of the desired product as a white solid.

Workup

  1. temperatureThe resulting mixture was heated to 70° for 15 h
  2. customthe isopropanol was removed by evaporation in vacuo
  3. filtrationThe resulting white precipitate was collected by filtration
  4. washwashed with isopropanol and ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a3d5ea0f67df454ebc8d67975d86b82a
Source dataset
uspto-grants-2002_03
Patent number
US06358980B1

Reaction notes

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