Methanol → 1-(3,4-Dimethylphenyl)-2,2-dimethylpropan-1-one

HRID 1974371Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1974371
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].[CH3:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[CH3:16])[C:10](Cl)=[O:11].CO.[Cl-].[NH4+]>O1CCCC1.C1(S[Cu])C=CC=CC=1>[CH3:6][C:7]1[CH:8]=[C:9]([C:10](=[O:11])[C:1]([CH3:4])([CH3:3])[CH3:2])[CH:13]=[CH:14][C:15]=1[CH3:16]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 27585353,4-Dimethylbenzoyl chlorideHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 154668571-(3,4-Dimethylphenyl)-2,2-dimethylpropan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178505381HCID 178505381, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

A suspension of 25.9 g. (0.15 mole) of phenyl thio copper in 1 liter dry tetrahydrofuran is cooled to -20° C. and treated by the dropwise addition of 120 ml. t-butyl lithium (0.149 mole, 1.24 M in pentane) for about 20 minutes maintaining the temperature at -20° C. The resulting green solution is stirred at -20° C. for 5 minutes and then cooled to -72° C. and treated by the dropwise addition of 17.8 g. (0.107 mole) 3,4-dimethyl-benzoyl chloride in 50 ml. tetrahydrofuran for about 20 minutes. The mixture is then stirred at -22° C. for 11/2 hours and then treated with 100 ml. methanol and allowed to warm to room temperature and then hydrolyzed by the addition of 250 ml. saturated ammonium chloride. The resulting solids are filtered and washed with tetrahydrofuran. The filtrate is dried over anhydrous magnesium sulfate, filtered and evaporated and the oil distilled to give 3',4' -dimethylpivalophenone; (b.p. 73°-76° C. at 0.1 mm).

Aufarbeitung

  1. additionA suspension of 25.9 g
  2. additiontreated by the dropwise addition of 120 ml
  3. temperaturecooled to -72° C.
  4. additiontreated by the dropwise addition of 17.8 g
  5. stirringThe mixture is then stirred at -22° C. for 11/2 hours
  6. additiontreated with 100 ml
  7. temperatureto warm to room temperature
  8. additionhydrolyzed by the addition of 250 ml
  9. filtrationThe resulting solids are filtered
  10. washwashed with tetrahydrofuran
  11. dry with materialThe filtrate is dried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. customevaporated
  14. distillationthe oil distilled

Quellen und Nachweise

ORD-Eintrag
ord-02aae9f3867c46ec8784a1ed07272163
Quelldatensatz
uspto-grants-1976_12
Patentnummer
US04000307

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