2,4-Dihydroxybenzaldehyde → HCID 10537643, Verbindung

HRID 322948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 322948
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl[CH2:14][C:15]1[CH:19]=[CH:18][S:17][CH:16]=1>CN(C)C=O>[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH2:14][C:15]2[CH:19]=[CH:18][S:17][CH:16]=2)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

5

Edukt 3

HCID 72132,4-DihydroxybenzaldehydeHCID 24758Sodium hydrideHCID 124874623-(Chloromethyl)thiophene

Produkt 1

HCID 10537643HCID 10537643, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 2,4-dihydroxybenzaldehyde (42.6 g) in dimethylformamide (250 mL) at ambient temperature is treated with sodium hydride (13.5 g; 60% w/v dispersion in mineral oil; 338 mmol), portionwise during 30 minutes. It is then treated with 3-chloromethylthiophene and the reaction mixture is heated at 60° C. for 3 hours. The mixture is concentrated in vacuo and the residue is partitioned between hydrochloric acid (200 mL; 0.5 N) and ethyl acetate (200 mL). The aqueous layer is extracted with ethyl acetate (3×100 mL) and the combined organic extracts are washed with brine (50 mL), dried over magnesium sulphate, filtered and the solvent is removed in vacuo. Flash chromatography on silica gel, using a mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate (4:1 v/v) as eluent, gives 2-hydroxy-4-(3-thienylmethoxy)benzaldehyde (11.8 g), in the form of a white solid.

Aufarbeitung

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe residue is partitioned between hydrochloric acid (200 mL; 0.5 N) and ethyl acetate (200 mL)
  3. extractionThe aqueous layer is extracted with ethyl acetate (3×100 mL)
  4. washthe combined organic extracts are washed with brine (50 mL)
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent is removed in vacuo
  8. additiona mixture of petroleum ether (b.p. 40-60° C.) and ethyl acetate (4:1 v/v) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-c8c18f4c75874b1a910d5d856be4a462
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211234B1

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