4-Toluenesulfonyl chloride → HCID 58633250, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence