Potassium Hydroxide → 2-Carboxy-2-(4-methoxybenzylthio)indan

HRID 37375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 37375
[C:1]([C:5]1([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)([O:3]C)=[O:2].[OH-].[K+]>C(O)C.O.O1CCCC1>[C:1]([C:5]1([S:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13]1)([OH:3])=[O:2]

Komponenten

6

Edukt 2

HCID 14797Potassium HydroxideHCID 152807342-(Carbomethoxy)-2-(4-methoxybenzylthio)indan

Produkt 1

HCID 152807352-Carboxy-2-(4-methoxybenzylthio)indanAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Dissolve 2-(carbomethoxy)-2-(4-methoxybenzylthio)indan (2.20 g, 3.55 mmol) in 95% ethanol (25 mL), water (12 mL) and tetrahydrofuran (15 mL). Treat with potassium hydroxide (1.3 g, 2 3 mmol) and stir at room temperature for 1 hour. Filter and evaporate the solvent in vacuo. Partition between water (125 mL) and ether (75 mL). Separate the aqueous phase and acidify with cold concentrated hydrochloric acid. Extract with methylene chloride (75 mL), dry (Na2SO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (2:1 hexane/ethyl acetate) to give 2-carboxy-2-(4-methoxybenzylthio)indan as a yellow solid (0.48 g, 43%).

Aufarbeitung

  1. filtrationFilter
  2. customevaporate the solvent in vacuo
  3. customPartition between water (125 mL) and ether (75 mL)
  4. customSeparate the aqueous phase
  5. extractionExtract with methylene chloride (75 mL)
  6. dry with materialdry (Na2SO4)
  7. customevaporate the solvent in vacuo
  8. customPurify by silica gel chromatography (2:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-59a33a6faa3c4cb4bbf81a1b1cabcf6a
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420271

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