Cornforth reagent → 4-Butyryl-2-hydroxy-benzoic acid methyl ester

HRID 1160794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160794
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:14])[CH2:11][CH2:12][CH3:13])=[CH:6][C:5]=1[OH:15].C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:14])[CH2:11][CH2:12][CH3:13])=[CH:6][C:5]=1[OH:15]

Komponenten

4

Edukt 2

HCID 2724130Cornforth reagentHCID 595180182-Hydroxy-4-(1-hydroxy-butyl)-benzoic acid methyl ester

Produkt 1

HCID 595180214-Butyryl-2-hydroxy-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To the solution of 2-hydroxy-4-(1-hydroxy-butyl)-benzoic acid methyl ester (132 mg, 0.59 mmol) in DCM (6 mL), is added PDC (245 mg, 1.1 mmol) in one portion. The reaction is stirred overnight. The reaction mixture is filtered through a silica gel plug using DCM as eluent. The filtrate is concentrated to give 4-butyryl-2-hydroxy-benzoic acid methyl ester as a white solid: 1H NMR (400 MHz, CDCl3) δ 10.77 (s, 1H), 7.92 (d, 1H, J=8.4 Hz), 7.52 (d, 1H, J=1.6 Hz), 7.44 (dd, 1H, J=1.6, 8 Hz), 3.99 (s, 3H), 2.93 (t, 2H, J=7.2 Hz), 1.76 (qt, 2H, J=7.6 Hz), 1.00 (t, 3H, J=7.6 Hz).

Aufarbeitung

  1. filtrationThe reaction mixture is filtered through a silica gel plug
  2. concentrationThe filtrate is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3f9688a133d74c52aca61d19467a0a7d
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816542B2

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