Hydrochloric Acid → p-Toluenesulfonic acid

HRID 1395636Notes

Reaction equation

HRID 1395636 reaction equation
CC1C(O)CC(=[O:5])C=1CC=C.C(N(CC)CC)C.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.Cl>C(Cl)Cl>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([OH:5])(=[O:27])=[O:26])=[CH:21][CH:20]=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 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-17 °C

Procedure

First, 8.6 g of (R) allethrolone and then 16 ml of triethylamine were added at -40° C. to 50 ml of methylene chloride and a solution of 21.4 g of p-toluene sulfonyl chloride in 150 ml of methylene chloride was added thereto over 15 minutes at -40° C. The mixture was stirred for 48 hours at -17° C. and was then poured into an aqueous iced 0.1 N hydrochloric acid solution. The mixture was stirred and the aqueous phase was extracted with ether. The ether extracts were washed with water and dried over magnesium sulfate to obtain 18.5 g of raw product. The latter was chromatographed over silica gel and was eluted with a 9-1 benzene-ethyl acetate mixture to obtain 3.7 g of p-toluene sulfonate of (R) allethrolone.

Workup

  1. stirringThe mixture was stirred
  2. extractionthe aqueous phase was extracted with ether
  3. washThe ether extracts were washed with water
  4. dry with materialdried over magnesium sulfate
  5. customto obtain 18.5 g of raw product
  6. customThe latter was chromatographed over silica gel
  7. washwas eluted with a 9-1 benzene-ethyl acetate mixture

Sources & evidence

ORD record
ord-5a234cd3d376497e951209d6f4f3bc52
Source dataset
uspto-grants-1980_05
Patent number
US04205008

Reaction notes

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