Hydrochloric Acid → HCID 23717474, compound

HRID 2287953Notes

Reaction equation

HRID 2287953 reaction equation
[CH3:1][CH:2]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].Cl[S:20]([OH:23])(=[O:22])=[O:21].Cl.C[O-].[Na+:27]>C(Cl)(Cl)Cl>[S:20]([O-:23])([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][CH2:15][CH2:16][CH2:17][CH3:18])(=[O:22])=[O:21].[Na+:27]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24638Chlorosulfonic acidHCID 10942334Sodium MethoxideHCID 18427308HCID 18427308, compound

Product 1

HCID 23717474HCID 23717474, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
27.5 °C

Procedure

Into a dried 1 L 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-methylhexadecanol (124 g, 0.484 mol), prepared as an intermediate in Example I. Chlorosulfonic acid (60 g, 0.509 mol) is slowly added to the stirred mixture while maintaining 25-30° C. temperature with a ice bath. Once HCl evolution has stopped (1 hr.) slowly add sodium methoxide (25% in methanol) while keeping temperature at 25-30° C. until an aliquot at 5% concentration in water maintains a pH of 10.5. To the mixture is added hot ethanol (55° C., 2 L). The mixture is vacuum filtered immediately. The filtrate is concentrated to a slurry on a rotary evaporator, cooled and then poured into 2 L of ethyl ether. The mixture is chilled to 5° C., at which point crystallization occurs, and vacuum filtered. The crystals are dried in a vacuum oven at 50° C. for 3 hrs. to obtain a white solid (136 g, 92% active by cat SO3 titration).

Workup

  1. customprepared as an intermediate in Example I
  2. customat 25-30° C.
  3. concentrationat 5% concentration in water
  4. additionTo the mixture is added hot ethanol (55° C., 2 L)
  5. filtrationfiltered immediately
  6. concentrationThe filtrate is concentrated to a slurry on a rotary evaporator
  7. temperaturecooled
  8. additionpoured into 2 L of ethyl ether
  9. temperatureThe mixture is chilled to 5° C., at which point crystallization
  10. filtrationvacuum filtered
  11. customThe crystals are dried in a vacuum oven at 50° C. for 3 hrs
  12. customto obtain a white solid (136 g, 92% active by cat SO3 titration)

Sources & evidence

ORD record
ord-3522896929d2441db1a8138aa0c2ab94
Source dataset
uspto-grants-2000_07
Patent number
US06087309

Reaction notes

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