Ammonia → 2-(2-Mercaptobenzyl)phenol

HRID 1987479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987479
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 (I) (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-5f52a805e826418eab7d7b4187cbb477
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07550505B2

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