Ethanol → Ethyl (4-methylbenzylthio)acetate

HRID 477332

Reaktionsgleichung

Reaktionsgleichung von HRID 477332
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].CC[O-].[Na+].C(O)C.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=1>ClCCl>[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][S:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 7721p-Xylyl bromideHCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxide

Produkt 1

HCID 4107274Ethyl (4-methylbenzylthio)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyl 2-mercaptoacetate (8.5 cc) is added in the course of 15 minutes at a temperature in the region of 20° C. to a stirred solution, through which a stream of nitrogen is passed, of a 2M ethanolic solution of sodium ethylate (37.5 cc) and ethanol (50 cc). The mixture is left with stirring for 15 minutes at the same temperature, and α-bromo-p-xylene (13.9 g) is then added in the course of 20 minutes at a temperature in the region of 20° C. Stirring is maintained for 60 minutes at this temperature, and the reaction mixture is then evaporated to dryness at 50° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue obtained is dissolved in dichloromethane (100 cc), and the organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). Ethyl (4-methylbenzylthio)acetate (15.6 g) is thereby obtained, and is used in the crude state in the subsequent syntheses.

Aufarbeitung

  1. waitThe mixture is left
  2. additionis then added in the course of 20 minutes at a temperature in the region of 20° C
  3. temperatureis maintained for 60 minutes at this temperature
  4. customthe reaction mixture is then evaporated to dryness at 50° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  5. customThe residue obtained
  6. dry with materialthe organic phase is dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)

Quellen und Nachweise

ORD-Eintrag
ord-5f945fb988944ca2b579be667497689b
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04886835

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