Hydrochloric Acid → Propyl p-toluenesulfonate

HRID 37781Notes

Reaction equation

HRID 37781 reaction equation
[CH2:1]([OH:4])[CH2:2][CH3:3].C(N(CC)CC)C.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.Cl>C(Cl)Cl>[S:18]([C:15]1[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=1)([O:4][CH2:1][CH2:2][CH3:3])(=[O:20])=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10311-PropanolHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 69035Propyl p-toluenesulfonateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 100 L glass, jacketed reactor was charged with 1-propanol (2.098 kg; 34.9 mol), triethylamine (4.585 kg; 45.3 mol; 1.3 equivalents) and DCM (20.1 L). The mixture was cooled to a temperature of about 5° C. to 15° C. and cautiously charged with a solution of p-toluenesulfonyl chloride (6 kg; 31.47 mol; 0.9 equivalents) in DCM (10.5 L) over 30 minutes. Once the addition was complete, the mixture was warmed to a temperature of about 18° C. to 22° C. and stirred for 12 hours. The reaction mixture was assayed by 1H NMR (in CDCl3) and deemed complete. HCl (6 N; 2.98 L) was cautiously charged while maintaining the temperature below 25° C. The aqueous phase was removed, and the organic phase was washed 2× with water (21 L each wash), dried with MgSO4, and filtered over Celite®. The filtered solids were then washed with DCM (4 L) and concentrated to a residue. The residue was dissolved in heptane and concentrated again to afford a final propyl tosylate product (6.385 kg, 95% yield).

Workup

  1. temperatureThe mixture was cooled to a temperature of about 5° C. to 15° C.
  2. additionOnce the addition
  3. temperaturethe mixture was warmed to a temperature of about 18° C. to 22° C.
  4. temperaturewhile maintaining the temperature below 25° C
  5. customThe aqueous phase was removed
  6. washthe organic phase was washed 2× with water (21 L each wash)
  7. dry with materialdried with MgSO4
  8. filtrationfiltered over Celite®
  9. washThe filtered solids were then washed with DCM (4 L)
  10. concentrationconcentrated to a residue
  11. dissolutionThe residue was dissolved in heptane
  12. concentrationconcentrated again

Sources & evidence

ORD record
ord-a3ae704d5b3b4c4cbd304866f54aa988
Source dataset
uspto-grants-2013_09
Patent number
US08524695B2

Reaction notes

Loading…