Acetic Acid → 3-Phenyl-3-buten-2-one

HRID 1024355

Reaktionsgleichung

Reaktionsgleichung von HRID 1024355
[C:1]1([CH2:7][C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C=O.N1CCCC[CH2:14]1.CC(O)=O>CO>[C:1]1([C:7](=[CH2:14])[C:8](=[O:10])[CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 7678PhenylacetoneHCID 8082Piperidine

Produkt 1

HCID 3247973-Phenyl-3-buten-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

1-Phenyl-propan-2-one (40.8 g) was dissolved in 200 ml of MeOH. Formaline (37%) (79 mL), piperidine (4 ml) and HOAc (4 ml) where added and de reaction was stirred for 3 h at 60° C. The reaction mixture was evaporated to dryness under reduced pressure. The residue was taken up in diethyl ether, and extracted with water. The organic layer was washed with 1M HCl, dried over MgSO4 and evaporated under reduced pressure to yield 36.3 g of a yellow liquid. 1H NMR (400 MHz, CDCl3) δ 2.41 (s, 3H), 5.87 (s, 1H), 6.18 (s, 1H), 7.24-7.40 (m, 5H).

Aufarbeitung

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. extractionextracted with water
  3. washThe organic layer was washed with 1M HCl
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4cbc3d269f8e4475b49876afa34949c9
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722887B2

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