Benzyl Bromide → 4-Benzyloxy-3-ethyl-5-methylbenzaldehyde

HRID 1094298Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094298
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])[CH:6]=[O:7])[CH3:2].[CH2:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17](C)[C:16]=1O)C.C(C1C=C(C=C(C)C=1O)C(NO)=N)C.C([O-])([O-])=O.[K+].[K+].C(Br)C1C=CC=CC=1>C(#N)C.O>[CH2:13]([O:11][C:10]1[C:9]([CH3:12])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH2:1][CH3:2])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

8

Edukt 5

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5193332-Ethyl-6-methylphenolHCID 231592103-Ethyl-4-hydroxy-5-methylbenzaldehydeHCID 178436626HCID 178436626, Verbindung

Produkt 1

HCID 866393484-Benzyloxy-3-ethyl-5-methylbenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3-ethyl-4-hydroxy-5-methyl-benzaldehyde (34.9 g, 0.213 mol, prepared from 2-ethyl-6-methyl-phenol according to the literature cited for 3-ethyl-4,N-dihydroxy-5-methyl-benzamidine) in acetonitrile (350 mL), K2CO3 (58.7 g, 0.425 mol) and benzylbromide (36.4 g, 0.213 mol) is added. The mixture is stirred at 60° C. for 2 h before it is cooled to rt, diluted with water and extracted twice with EA. The org. extracts are washed with water and concentrated to give crude 4-benzyloxy-3-ethyl-5-methyl-benzaldehyde (45 g) as an orange oil. 1H NMR (CDCl3): δ 1.29 (t, J=7.5 Hz, 3H), 2.40 (s, 3H), 2.77 (q, J=7.8 Hz, 2H), 4.90 (s, 2H), 7.31-7.52 (m, 5 H), 7.62 (d, J=1.5 Hz, 1H), 7.66 (d, J=1.8 Hz, 1H), 9.94 (s, 1H).

Aufarbeitung

  1. temperatureis cooled to rt
  2. extractionextracted twice with EA
  3. washextracts are washed with water
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7d14cba212c2442c95d563ddc363546a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133910B2

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