Acetovanillone → 2',3'-Dihydroxyacetophenone

HRID 38631

Reaktionsgleichung

Reaktionsgleichung von HRID 38631
[CH3:1][C:2]([C:4]1[CH:12]=[CH:11][C:9](O)=[C:6]([O:7]C)[CH:5]=1)=[O:3].C([O-])([O-])=[O:14].[K+].[K+].C(Br)C1C=CC=CC=1>CC#N>[CH3:1][C:2]([C:4]1[CH:12]=[CH:11][CH:9]=[C:6]([OH:7])[C:5]=1[OH:14])=[O:3]

Komponenten

5

Edukt 3

HCID 2214AcetovanilloneHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Produkt 1

HCID 64291102',3'-DihydroxyacetophenoneAusbeute 70,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of acetovanillone (33) (4.70 g, 28.3 mmol) in MeCN (60 mL) was added K2CO3 (8.05 g, 58.3 mmol) and KI (0.20 g, 1.2 mmol). The mixture was stirred under N2 atmosphere and benzyl bromide (34) (4.0 mL, 34 mmol) was added dropwise. The reaction mixture was reflux for 24 h and then cooled to 25° C., then resulting precipitate was filtered off. The filtrate was evaporated and purified by column chromatography (SiO2, n-hexane: CH2Cl2=1:2) to give 30. White solid; yield: 70.3%; mp 87-88° C.; 1H-NMR (CDCl3. 200 MHz): δ 2.51 (s, 3H), 3.91 (s, 3H), 5.20 (s, 2H), 6.86 (d, J=8.2 Hz, 1H), 7.21-7.55 (m, 7H); 13C-NMR (CDCl3, 50 MHz): δ 26.19, 56.05, 70.79, 110.53, 112.13, 123.07, 127.18, 128.10, 128.68, 130.72, 136.28, 149.49, 152.41, 196.80; Anal. calcd for C16H16O3: C, 74.98; H, 6.29. Found: C, 75.02; H, 6.25.

Aufarbeitung

  1. temperatureThe reaction mixture was reflux for 24 h
  2. customresulting precipitate
  3. filtrationwas filtered off
  4. customThe filtrate was evaporated
  5. custompurified by column chromatography (SiO2, n-hexane: CH2Cl2=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-904a19f9ad764a429ae73edd9fd181c0
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524740B2

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