Methanol → 5-Carboxy-3-(2,4-dichlorobenzyl)-2-methylbenzo[b]thiophene

HRID 1072833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1072833
[Cl:1][C:2]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:3]=1[CH2:4][C:5]1[C:6]2[CH:14]=[C:13]([C:15]([O:17]C)=[O:16])[CH:12]=[CH:11][C:7]=2[S:8][C:9]=1[CH3:10].CO.[OH-].[Na+]>O1CCCC1>[C:15]([C:13]1[CH:12]=[CH:11][C:7]2[S:8][C:9]([CH3:10])=[C:5]([CH2:4][C:3]3[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:2]=3[Cl:1])[C:6]=2[CH:14]=1)([OH:17])=[O:16]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 223881313-(2,4-Dichlorobenzyl)-5-(methoxycarbonyl)-2-methylbenzo[b]thiophene

Produkt 1

HCID 223878405-Carboxy-3-(2,4-dichlorobenzyl)-2-methylbenzo[b]thiophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 3-(2,4-Dichlorobenzyl)-5-(methoxycarbonyl)-2-methylbenzo[b]thiophene (0.52 g, 1.42 mmol), methanol (5 ml), tetrahydrofuran (5 ml) and 2M aqueous sodium hydroxide solution (7 ml) was refluxed under heating for 1 hr. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. Then, the mixture was acidified with 3N hydrochloric acid and the precipitate was extracted from hot ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure to give the objective compound (0.45 g, 90% by two steps) as colorless crystals.

Aufarbeitung

  1. temperaturewas refluxed
  2. temperatureunder heating for 1 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. extractionthe precipitate was extracted from hot ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe desiccant was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customto give the objective compound (0.45 g, 90% by two steps) as colorless crystals

Quellen und Nachweise

ORD-Eintrag
ord-9eb791c264914eadb4047a40ea2683fc
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911469B2

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