Sulfuric Acid → Tetrabutylammonium Naphthalene-1-sulfinate

HRID 15613

Reaction equation

HRID 15613 reaction equation
[C:1]1([S:11](Cl)(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[O-]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+].OS(O)(=O)=O.[OH-].[CH2:32]([N+:36]([CH2:45][CH2:46][CH2:47][CH3:48])([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH3:35]>CO.O>[C:1]1([S:11]([O-:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:45]([N+:36]([CH2:32][CH2:33][CH2:34][CH3:35])([CH2:37][CH2:38][CH2:39][CH3:40])[CH2:41][CH2:42][CH2:43][CH3:44])[CH2:46][CH2:47][CH3:48]

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 24437Sodium SulfiteHCID 665601-Naphthalenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2723671Tetrabutylammonium Hydroxide

Product 1

HCID 22055080Tetrabutylammonium Naphthalene-1-sulfinate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
65 °C

Procedure

A round bottom flask was charged with 1-naphthalenesulfonyl chloride (20.0 g), Na2SO3 (33.36 g), NaHCO3 (22.24 g) and deionized water (350 mL). The mixture was stirred and heated to 65° C. under a nitrogen atmosphere for 2 hours, after which time the mixture was allowed to cool to room temperature and was then further cooled in a refrigerator. The cold mixture was acidified with concentrated H2SO4 which resulted in the formation of a precipitate. The mixture was extracted three times with 100 mL of ethyl acetate. The organic extracts were combined and the solvent was removed with a rotary evaporator to give a colorless solid that was then dissolved in 240 mL of 1:1 (v/v) methanol-deionized water in a beaker. The solution was titrated with a solution of 40% aqueous tetrabutylammonium hydroxide until the pH of the solution was 7.2. The solvent was removed with a rotary evaporator and the product was further dried in a vacuum oven at room temperature to afford 36.4 g of a yellow waxy solid.

Workup

  1. temperatureto cool to room temperature
  2. temperaturewas then further cooled in a refrigerator
  3. customresulted in the formation of a precipitate
  4. extractionThe mixture was extracted three times with 100 mL of ethyl acetate
  5. customthe solvent was removed with a rotary evaporator
  6. customto give a colorless solid
  7. customThe solvent was removed with a rotary evaporator
  8. customthe product was further dried in a vacuum oven at room temperature
  9. customto afford 36.4 g of a yellow waxy solid

Sources & evidence

ORD record
ord-ac3c4e7ce53e49939894da1a164c3f08
Source dataset
uspto-grants-2010_06
Patent number
US07732633B2

Linked notes

Loading…