Sodium Hydroxide → HCID 86621004, compound

HRID 1677903Notes

Reaction equation

HRID 1677903 reaction equation
Cl[CH:2]([CH2:12][S:13]([F:18])([F:17])([F:16])([F:15])[F:14])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8]([OH:11])(=[O:10])=[O:9].[OH-].[Na+:20]>O1CCCC1>[F:18][S:13]([F:14])([F:15])([F:16])([F:17])[CH:12]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8]([O-:11])(=[O:9])=[O:10].[Na+:20]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 59745703HCID 59745703, compound

Product 1

HCID 86621004HCID 86621004, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
97 °C

Procedure

10g (29.35 mmol; 1 eq) of sulfonic acid from Example 6b are suspended in 400 ml of tetrahydrofuran in a 500 ml flask, and 11.74 g (293.5 mmol; 10 eq) of sodium hydroxide are subsequently added. The reaction mixture is heated under reflux for 10 h, cooled and acidified, and the sulfonic acid is separated off from the aqueous phase by repeated extraction with methyl t-butyl ether. The organic phase is subsequently washed and evaporated to dryness. The crude sulfonic acid is suspended in 100 ml of ethanol, 1.4 g (35.22 mmol; 1.2 eq) of sodium hydroxide are added, and the mixture is heated at 97° C. for 1 h. After the suspension has been cooled, crystals deposit, which are filtered off and dried.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 10 h
  3. temperaturecooled
  4. customthe sulfonic acid is separated off from the aqueous phase by repeated extraction with methyl t-butyl ether
  5. washThe organic phase is subsequently washed
  6. customevaporated to dryness
  7. temperatureAfter the suspension has been cooled
  8. filtrationcrystals deposit, which are filtered off
  9. customdried

Sources & evidence

ORD record
ord-d56e3ce8d194454698e5cd097a27e074
Source dataset
uspto-grants-2011_08
Patent number
US08008358B2

Reaction notes

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