Hydrochloric Acid → p-Toluenesulfonic acid

HRID 1763408Notes

Reaction equation

HRID 1763408 reaction equation
C(N(CC)CC)C.[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1.CC1C(O)CC(=[O:23])C=1CC=C.Cl>O1CCCC1>[CH3:18][C:8]1[CH:13]=[CH:12][C:11]([S:14]([OH:23])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 110832-Cyclopenten-1-one, 4-hydroxy-3-methyl-2-(2-propen-1-yl)-2×

Product 1

HCID 6101p-Toluenesulfonic acidYield 51.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

11.6 g of triethylamine and then 21.9 g of p-toluene sulfonyl chloride were added at -50° C under an inert atmosphere to a mixture of 11.6 g of (R) allethrolone in 100 ml of tetrahydrofuran and the mixture was stirred for 48 hours at 5° C after which it was poured with stirring into aqueous 0.1N hydrochloric acid solution. The aqueous phase was extracted with chloroform and the organic extracts were washed with water, dried and evaporated to dryness. The 29 g of residue was chromatographed over silica gel and was eluted with a 95-5 benzene-ethyl acetate mixture to obtain 6.8 g of p-toluene sulfonate of (R) allethrolone.

Workup

  1. additionwas poured
  2. extractionThe aqueous phase was extracted with chloroform
  3. washthe organic extracts were washed with water
  4. customdried
  5. customevaporated to dryness
  6. customThe 29 g of residue was chromatographed over silica gel
  7. washwas eluted with a 95-5 benzene-ethyl acetate mixture

Sources & evidence

ORD record
ord-8aec1e8f30174c50a4afca055833f4b6
Source dataset
uspto-grants-1978_09
Patent number
US04111994

Reaction notes

Loading…