Benzaldehyde → 2,4-Pentanedione, 3-(phenylmethylene)-

HRID 77637

Reaktionsgleichung

Reaktionsgleichung von HRID 77637
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[CH:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>C1C=CC=CC=1.N1CCCCC1.C(O)(=O)C>[CH:8](=[C:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

7

Edukt 3

HCID 240BenzaldehydeHCID 962WaterHCID 31261Acetylacetone

Produkt 1

HCID 957822,4-Pentanedione, 3-(phenylmethylene)-Ausbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidKatalysatorHCID 8082PiperidineKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

2,4-Pentanedione (2, 4.10 ml, 39.2 mmol) and benzaldehyde (1b, 4.06 ml, 40.0 mmol) were stirred in benzene (10 ml). Piperdine (3 drops) and glacial acetic acid (6 drops) were added and the mixture refluxed with a Dean-Stark water trap for 3 hr. The resulting mixture was cooled to room temperature, extracted into ethyl ether, washed with hydrochloric acid (1 N), saturated sodium bicarbonate, hydrochloric acid (1 N) and twice with water. The organic layer was dried over magnesium sulfate, filtered and evaporated to afford an oil. The crude oil was distilled bulb to bulb to give 7.03 g (95%) of a yellow oil; [expected mp 165-167° C.]; 1H NMR: δ 2.24 (s, 3H), 2.38 (s, 3H), 7.35 (s, 5H), 7.45 (s, 1H); 13C NMR: δ 26.5, 31.6, 128.9, 129.6, 130.5, 132.8, 139.6, 142.7, 196.2, 205.3.

Aufarbeitung

  1. extractionextracted into ethyl ether
  2. washwashed with hydrochloric acid (1 N), saturated sodium bicarbonate, hydrochloric acid (1 N) and twice with water
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto afford an oil
  7. distillationThe crude oil was distilled bulb to bulb

Quellen und Nachweise

ORD-Eintrag
ord-8755114f947d4444af80e019f14ce045
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841326B2

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