Ammonia → 2-(2-Mercaptobenzyl)phenol

HRID 1158202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158202
C[S:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12].N.[Na].[NH4+].[Cl-]>CCCCCC.C(OCC)(=O)C.C1COCC1>[SH:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12]

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 686436452-(2-(Methylthio)benzyl)phenol

Produkt 1

HCID 686436382-(2-Mercaptobenzyl)phenolAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 0.68 g 2-(2-(methylthio)benzyl)phenol (1) (2.96 mmol) in 4 ml freshly distilled THF at −78° C. was added 8 mL condensed ammonia followed by 0.15 g sodium. The blue solution was stirred for 2 hours at −78° C. before the mixture was warmed to ambient temperature. The reaction was allowed to stir overnight before NH4Cl was added until neutral. The mixture was extracted with ethyl acetate and the combined organic extracts washed with brine, dried over magnesium sulfate and concentrated. Flash silica chromatography (hexane:ethyl acetate 80:20) afforded 0.457 g product (2.12 mmol, 71% yield).

Aufarbeitung

  1. temperaturewas warmed to ambient temperature
  2. additionwas added until neutral
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic extracts washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ff16a56cd9b941e78070b4fd8d97bcb5
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807713B2

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