Hydrochloric Acid → HCID 13298051, compound

HRID 2309762Notes

Reaction equation

HRID 2309762 reaction equation
[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.Cl>N1C=CC=CC=1>[S:30]([O:11][CH2:10][CH2:9][C:8]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:27]1[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 13298050HCID 13298050, compound

Product 1

HCID 13298051HCID 13298051, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The reaction is performed under dry conditions. 30.0 g of 1,1,2-triphenyl-1-butene-4-ol are dissolved in 100 ml of dry pyridine. Then with stirring and cooling the mixture on ice, 57.0 g of 4-toluenesulfonic acid chloride in 50 ml of dry pyridine are added dropwise to the mixture. The mixture is stirred for 6 h at 0° C. Then 250 ml of ice-cold water and 750 ml of cold 2M hydrochloric acid are added. The precipitate is collected by filtration and washed with water. Finally the product is recrystallized from ethanol. The yield is 36.8 g (81%) of a product having m.p. 137°-9° C.

Workup

  1. additionare added dropwise to the mixture
  2. stirringThe mixture is stirred for 6 h at 0° C
  3. filtrationThe precipitate is collected by filtration
  4. washwashed with water
  5. customFinally the product is recrystallized from ethanol

Sources & evidence

ORD record
ord-9ef4198d7c704971ac109bba712edc39
Source dataset
uspto-grants-1987_09
Patent number
US04696949

Reaction notes

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