Hydrochloric Acid → HCID 23704462, compound

HRID 1976539Notes

Reaction equation

HRID 1976539 reaction equation
[CH3:1][CH:2]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].Cl[S:17]([OH:20])(=[O:19])=[O:18].Cl.C[O-].[Na+:24]>C(Cl)(Cl)Cl>[S:17]([O-:20])([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]([CH3:1])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])(=[O:19])=[O:18].[Na+:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24638Chlorosulfonic acidHCID 10942334Sodium MethoxideHCID 18328642HCID 18328642, compound

Product 1

HCID 23704462HCID 23704462, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
27.5 °C

Procedure

Into a dried 1L 3 neck round bottom flask fitted with a nitrogen inlet, dropping funnel, thermometer, mechanical stirring and nitrogen outlet is added chloroform (300 ml) and 7-methyltridecanol (107 g, 0.5 mol), prepared as an intermediate in Example I. Chlorosulfonic acid (61.3 g, 0.52 mol) is slowly added to the stirred mixture while maintaining 25-30° C. temperature with an ice bath. Once HCl evolution has stopped (1 hr.) slowly add sodium methoxide (25% in methanol) while keeping temperature at 25-30° C. until a aliquot at 5% concentration in water maintains a pH of 10.5. To the mixture is added methanol (1L) and 300 ml of 1-butanol. Vacuum filter off the inorganic salt precipitate and remove methanol from the filtrate on a rotary evaporator. Cool to room temperature, add 1L of ethyl ether and let stand for 1 hour. The precipitate is collected by vacuum filtration. The product is dried in a vacuum oven at 50C for 3 hrs. to obtain a white solid (76 g, 90% active by cat SO3 titration).

Workup

  1. dry with materialInto a dried 1L 3 neck round bottom flask
  2. customfitted with a nitrogen inlet
  3. customprepared as an intermediate in Example I
  4. customat 25-30° C.
  5. concentrationat 5% concentration in water
  6. additionTo the mixture is added methanol (1L) and 300 ml of 1-butanol
  7. filtrationVacuum filter off the inorganic salt precipitate
  8. customremove methanol from the filtrate
  9. customon a rotary evaporator
  10. temperatureCool to room temperature
  11. additionadd 1L of ethyl ether
  12. filtrationThe precipitate is collected by vacuum filtration
  13. dry with materialThe product is dried in a vacuum oven at 50C for 3 hrs
  14. customto obtain a white solid (76 g, 90% active by cat SO3 titration)

Sources & evidence

ORD record
ord-8f3324123e034690a8d511c8519ca563
Source dataset
uspto-grants-2001_05
Patent number
US06228829B1

Reaction notes

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