Water → HCID 19861815, Verbindung

HRID 1165446

Reaktionsgleichung

Reaktionsgleichung von HRID 1165446
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5].[Br:16]N1C(=O)CCC1=O.O>C(Cl)Cl>[OH:1][C:2]1[C:9]([Br:16])=[C:8]([O:10][CH3:11])[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 198618272-Hydroxy 4-methoxy-5-(1,1-dimethylethyl)benzaldehyde

Produkt 1

HCID 19861815HCID 19861815, VerbindungAusbeute 69,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2.56 g (12.3 mmol) of 2-hydroxy 4-methoxy-5-(1,1-dimethylethyl)benzaldehyde and 2.19 g (12.3 mmol) of N-bromosuccinimide in 20 ml of methylene chloride was stirred for 6 hours. Water (50 ml) was added. The organic phase was dried and evaporated. The residue was chromatographed on silica gel (36 g) using 2:98 (v/v) ether/hexane as eluent. There was obtained 2.45 g (8.53 mmol, 69%) of 2-hydroxy-3-bromo-4-methoxy-(1,1-dimethylethyl)benzaldehyde as white crystals after crystallization from cyclohexane; mp 123°-124° C.

Aufarbeitung

  1. customThe organic phase was dried
  2. customevaporated
  3. customThe residue was chromatographed on silica gel (36 g)

Quellen und Nachweise

ORD-Eintrag
ord-5402824a46e04fb58d264b6117d78d30
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04910202

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