Hydrochloric Acid → 2,3-Epoxypropyl 3-(phenylthio)propionate

HRID 126673

Reaktionsgleichung

Reaktionsgleichung von HRID 126673
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8]([O:12][CH2:13][CH:14]1[O:16][CH2:15]1)(=[O:11])[CH:9]=[CH2:10].[OH-].[K+].C(S)(S)CC.Cl>CC(O)C.O>[C:1]1([S:7][CH2:10][CH2:9][C:8]([O:12][CH2:13][CH:14]2[O:16][CH2:15]2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 7836Glycidyl acrylateHCID 7969ThiophenolHCID 14797Potassium Hydroxide2×HCID 64285461,1-Propanedithiol

Produkt 1

HCID 202874532,3-Epoxypropyl 3-(phenylthio)propionate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

2,3-epoxypropyl 3-(phenylthio)propionate was prepared by adding 11.0 grams (0.1 moles) of benzenethiol to a solution of 12.8 grams of 2,3-epoxypropyl acrylate with 10 drops of Triton B® in 50 milliliters of 2-propanol. The addition was carried out over a period of 5 minutes during which the temperature of the reaction mixture rose to 54° C. The mixture was then stirred for 3.5 hours at ambient temperature. To this reaction mixture was added 0.5 grams of potassium hydroxide. After the potassium hydroxide had dissolved there was added 5.4 grams of propanedithiol and the reaction mixture was stirred for 3.5 hours. The mixture was then poured into a solution of 5 milliliters of concentrated hydrochloric acid in 100 milliliters of water. The organic oil was separated by extraction with toluene and toluene was then removed from the extract by rotary evaporator. There was obtained 26.6 grams (0.091 moles) of a viscous liquid shown by its NMR spectrum to be 2,9 -dihydroxy-4,7-dithia-5-methyldecamethylene bis[3-(phenylthio)propionate].

Aufarbeitung

  1. additionThe addition
  2. customrose to 54° C
  3. stirringthe reaction mixture was stirred for 3.5 hours
  4. customThe organic oil was separated by extraction with toluene and toluene
  5. customwas then removed from the
  6. extractionextract by rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-8dcfcab87e294d2abdffaaa2b37c6418
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254020

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