4-Toluenesulfonyl chloride → HCID 58633250, compound

HRID 2368787Notes

Reaction equation

HRID 2368787 reaction equation
[Cl-].[Li+].C([Mg]Cl)=C.[S:7](Cl)([C:10]1[CH:16]=[CH:15][C:13]([CH3:14])=[CH:12][CH:11]=1)(=[O:9])=[O:8].[CH3:18][C@@H:19]([OH:23])[CH2:20][CH:21]=[CH2:22]>C1COCC1.[Cu]Cl>[C:13]1([CH3:14])[CH:15]=[CH:16][C:10]([S:7]([O:23][C@@H:19]([CH2:20][CH:21]=[CH2:22])[CH3:18])(=[O:9])=[O:8])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 433294Lithium ChlorideHCID 6999724(2R)-pent-4-en-2-olHCID 178461836HCID 178461836, compound

Product 1

HCID 58633250HCID 58633250, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Copper(I) chloride (645 g, 6.52 mol) and lithium chloride (550 g, 12.9 mol) were dissolved in THF (140 L) and cooled to 0° C. Vinyl magnesium chloride (349 kg, 633 mol, 16.5% in THF) was added slowly, maintaining the temperature below 5° C. The mixture was cooled to −15° C. A cooled solution of R-propylene oxide (37.8 kg, 651 mol) in THF (900 L) was added slowly, maintaining the temperature below −15° C. The reaction mixture was stirred until more than 98.5% of R-propylene oxide had been consumed (using GC). The mixture was added slowly to a cooled solution of TsCl (127 kg, 664 mol) in THF (470 L). The mixture was heated to ambient temperature and stirred until more than 98% of the 4-penten-2(R)-ol had been consumed (using GC). The reaction mixture was transferred to a mixture of water (630 L) and MTBE (280 L). Hydrochloric acid was added until pH≦2.5. The phases were separated and the aqueous phase was washed with MTBE. The combined organic phases were washed with aqueous sodium chloride solution and the organic phase was distilled to remove MTBE, to yield (R)-4-penten-2-yl p-toluenesulfonate in a THF solution (190 L). THF (120 L) is then added to the solution.

Workup

  1. temperaturemaintaining the temperature below 5° C
  2. temperatureThe mixture was cooled to −15° C
  3. temperaturemaintaining the temperature below −15° C
  4. customhad been consumed (using GC)
  5. temperatureThe mixture was heated to ambient temperature
  6. customhad been consumed (using GC)
  7. additionThe reaction mixture was transferred to a mixture of water (630 L) and MTBE (280 L)
  8. additionHydrochloric acid was added until pH≦2.5
  9. customThe phases were separated
  10. washthe aqueous phase was washed with MTBE
  11. washThe combined organic phases were washed with aqueous sodium chloride solution
  12. distillationthe organic phase was distilled
  13. customto remove MTBE

Sources & evidence

ORD record
ord-1514832dea7e4ab8ad821f2da111db02
Source dataset
uspto-grants-2014_04
Patent number
US08703802B2

Reaction notes

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