PROPYL P-TOLUENESULFONATE synthesis
- Product Name:PROPYL P-TOLUENESULFONATE
- CAS Number:599-91-7
- Molecular formula:C10H14O3S
- Molecular Weight:214.28
Yield:599-91-7 95%
Reaction Conditions:
with triethylamine in dichloromethane at 5 - 22; for 12.5 h;Industry scale;
Steps:
16
[00263] EXAMPLE 16 - Industrial scale preparation of propyl tosylate:; 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 5oC to 15oC and cautiously charged with a solution of /Moluenesulfonyl 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 18oC to 22oC and stirred for 12 hours. The reaction mixture was assayed by 1H NMR (in CDCI3) and deemed complete. HCl (6 N; 2.98 L) was cautiously charged while maintaining the temperature below 25oC. The aqueous phase was removed, and the organic phase was washed 2 X with water (21 L each wash), dried with MgSC>4, 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).
References:
WO2010/22140,2010,A1 Location in patent:Page/Page column 101
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