4-Methylbenzenethiol → Ethyl 2,2-bis(4-methylthiophenoxy)acetate

HRID 28115

Reaktionsgleichung

Reaktionsgleichung von HRID 28115
[Na].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([SH:9])=[CH:5][CH:4]=1.Cl[CH:11](Cl)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>CO.C(OCC)C>[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH:11]([S:9][C:6]2[CH:7]=[CH:8][C:3]([CH3:2])=[CH:4][CH:5]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 78114-MethylbenzenethiolHCID 10808Ethyl dichloroacetateHCID 5360545Sodium

Produkt 1

HCID 13107767Ethyl 2,2-bis(4-methylthiophenoxy)acetateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel3×HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Sodium (3.54 g) is dissolved in methanol (140 cc) and a solution of 4-methylthiophenol (21.8 g) in methanol (25 cc) is added. The mixture is stirred for 1 hour at 20° C. and a solution of ethyl dichloroacetate (12.5 g) in methanol (30 cc) is then added. The mixture is allowed to cool, the white precipitate obtained is filtered off, and the filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C. The oil obtained is taken up in diethyl ether (250 cc) and washed four times with N sodium hydroxide solution (50 cc each time) and four times with distilled water (50 cc each time). The ethereal phase is dried over anhydrous sodium sulphate, filtered, treated with animal charcoal, filtered and concentrated to dryness under reduced pressure (20 mmHg) at 40° C. Ethyl 2,2-bis(4-methylthiophenoxy)acetate (18 g) is thus obtained as a yellow oil.

Aufarbeitung

  1. temperatureto cool
  2. customthe white precipitate obtained
  3. filtrationis filtered off
  4. concentrationthe filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C
  5. customThe oil obtained
  6. washwashed four times with N sodium hydroxide solution (50 cc each time) and four times with distilled water (50 cc each time)
  7. dry with materialThe ethereal phase is dried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. additiontreated with animal charcoal
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (20 mmHg) at 40° C

Quellen und Nachweise

ORD-Eintrag
ord-6bb31a9cb3cd4b5eaac488e1d6f003df
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04225589

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