P-Cresol → Ethyl 2,2-bis(4-methylphenoxy)acetate

HRID 28114

Reaktionsgleichung

Reaktionsgleichung von HRID 28114
[Na].[CH:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[CH:3]=1.Cl[CH:11](Cl)[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C.C(OCC)C>[CH3:9][C:4]1[CH:5]=[CH:6][C:7]([O:8][CH:11]([O:8][C:7]2[CH:2]=[CH:3][C:4]([CH3:9])=[CH:5][CH:6]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:2][CH:3]=1

Komponenten

6

Edukt 3

HCID 2879P-CresolHCID 10808Ethyl dichloroacetateHCID 5360545Sodium

Produkt 1

HCID 23338923Ethyl 2,2-bis(4-methylphenoxy)acetateAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel3×HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

Sodium (5.7 g) is dissolved in ethanol (160 cc), and a solution of para-cresol (27 g) in ethanol (20 cc) is added. The mixture is stirred for 1 hour at 20° C. and ethyl dichloroacetate (20 g) in solution in ethanol (20 cc) is then added. The mixture is heated under reflux for 20 hours and then 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 thus obtained is taken up in diethyl ether (300 cc) and washed twice with N sodium hydroxide solution (100 cc each time) and twice with distilled water (100 cc each time). The ethereal phase is then dried over anhydrous sodium sulphate, filtered, and concentrated to dryness under reduced pressure (20 mmHg) at 40° C. Ethyl 2,2-bis(4-methylphenoxy)acetate (29 g) is thus obtained as a yellow oil.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 20 hours
  3. temperatureto cool
  4. customThe white precipitate obtained
  5. filtrationis filtered off
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (20 mmHg) at 40° C
  7. customThe oil thus obtained
  8. washwashed twice with N sodium hydroxide solution (100 cc each time) and twice with distilled water (100 cc each time)
  9. dry with materialThe ethereal phase is then dried over anhydrous sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness under reduced pressure (20 mmHg) at 40° C

Quellen und Nachweise

ORD-Eintrag
ord-b1d0998d3cf545b793e561524dc0c9a6
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04225589

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