Hydrochloric Acid → HCID 73437352, compound

HRID 1976537Notes

Reaction equation

HRID 1976537 reaction equation
[CH3:1][CH:2]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].ClS(O)(=O)=O.Cl.C[O-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][CH:2]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH:7]=[CH:8][OH:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24638Chlorosulfonic acidHCID 10942334Sodium MethoxideHCID 18328605HCID 18328605, compound

Product 1

HCID 73437352HCID 73437352, 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-methylundecanol (93 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., 2L). The mixture is vacuum filtered immediately. The filtrate is concentrated to a slurry on a rotary evaporator, cooled and then poured into 2L 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.

Workup

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

Sources & evidence

ORD record
ord-f52a2b19fe1745a09875a9cb452daef0
Source dataset
uspto-grants-2001_05
Patent number
US06228829B1

Reaction notes

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