Hydrochloric Acid → Sodium 7-methylheptadecyl sulfate

HRID 376242Notes

Reaction equation

HRID 376242 reaction equation
[CH3:1][CH:2]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].Cl[S:21]([OH:24])(=[O:23])=[O:22].Cl.C[O-].[Na+:28]>C(Cl)(Cl)Cl>[S:21]([O-:24])([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][CH2:18][CH3:19])(=[O:23])=[O:22].[Na+:28]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24638Chlorosulfonic acidHCID 10942334Sodium MethoxideHCID 18427309HCID 18427309, compound

Product 1

HCID 23717473Sodium 7-methylheptadecyl sulfate

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-Methylheptadecanol (102 g, 0.378 mol), prepared as an intermediate in Example III. Chlorosulfonic acid (46.7 g, 0.40 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 methanol (45° C.,1 L) to dissolve the branched sulfate followed immediately by vacuum filtration to remove the inorganic salt precipitate and repeated a second time. The filtrate is then cooled to 5° C. at which time 1 L of ethyl ether is added and let stand for 1 hour. The precipitate is collected by vacuum filtration. The product is dried in a vacuum oven at 50° C. for 3 hrs. to obtain a white solid (89 g, 88% active by cat SO3 titration). HNMR of the final product (in deuterium oxide) indicates a CH2 --OSO3 -- triplet at the 3.8 ppm resonance, CH2 --CH2 --OSO3 -- multiplet at the 1.5 ppm resonance, CH2 of the alkyl chain at the 0.9-1.3 ppm resonance and CH--CH3 branch point overlapping the R--CH2CH3 terminal methyl group at the 0.8 ppm resonance. Mass spectrometry data shows a molecular ion peak with a mass of 349.1 corresponding to the 7-methylheptadecyl sulfate ion. Also shown is the methyl branch at the 7 position due to the loss of 29 mass units at that position.

Workup

  1. customprepared as an intermediate in Example III
  2. customat 25-30° C.
  3. concentrationat 5% concentration in water
  4. additionTo the mixture is added hot methanol (45° C.,1 L)
  5. dissolutionto dissolve the branched sulfate
  6. filtrationfollowed immediately by vacuum filtration
  7. customto remove the inorganic salt precipitate
  8. temperatureThe filtrate is then cooled to 5° C. at which time 1 L of ethyl ether
  9. additionis added
  10. filtrationThe precipitate is collected by vacuum filtration
  11. customThe product is dried in a vacuum oven at 50° C. for 3 hrs
  12. customto obtain a white solid (89 g, 88% active by cat SO3 titration)

Sources & evidence

ORD record
ord-04061928d6f84ef99af13c649845d4d7
Source dataset
uspto-grants-2000_02
Patent number
US06020303

Reaction notes

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