Hydrochloric Acid → HCID 23704463, compound

HRID 1249668Notes

Reaction equation

HRID 1249668 reaction equation
[CH3:1][CH:2]([CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].Cl[S:16]([OH:19])(=[O:18])=[O:17].Cl.C[O-].[Na+:23]>C(Cl)(Cl)Cl>[S:16]([O-:19])([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][CH3:14])(=[O:18])=[O:17].[Na+:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24638Chlorosulfonic acidHCID 10942334Sodium MethoxideHCID 15569714HCID 15569714, compound

Product 1

HCID 23704463HCID 23704463, 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 siring and nitrogen outlet is added chloroform (300 ml) and 7-methyldodecanol (100 g, 0.5 mol). 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 50C for 3 hrs. to obtain a white solid (119 g, 92% active by cat SO3 titration).

Workup

  1. customat 25-30° C.
  2. concentrationat 5% concentration in water
  3. additionTo the mixture is added hot ethanol (55° C., 2 L)
  4. filtrationfiltered immediately
  5. concentrationThe filtrate is concentrated to a slurry on a rotary evaporator
  6. temperaturecooled
  7. additionpoured into 2 L of ethyl ether
  8. temperatureThe mixture is chilled to 5° C., at which point crystallization
  9. filtrationvacuum filtered
  10. dry with materialThe crystals are dried in a vacuum oven at 50C for 3 hrs
  11. customto obtain a white solid (119 g, 92% active by cat SO3 titration)

Sources & evidence

ORD record
ord-f2c9f473c417435697ce305e170996f4
Source dataset
uspto-grants-2002_01
Patent number
US06335312B1

Reaction notes

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