Water → 4-(Ethylthio)benzyl alcohol

HRID 257848

Reaktionsgleichung

Reaktionsgleichung von HRID 257848
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([S:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=1)[CH3:8].[OH-].[Na+].O>O1CCCC1>[CH2:7]([S:9][C:10]1[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=1)[CH3:8]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 832314-(Ethylthio)benzoic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 5336384-(Ethylthio)benzyl alcoholAusbeute 86,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The starting 4-(ethylthio)benzyl alcohol was prepared as follows. A mixture of lithium aluminum hydride (5.2 g) and tetrahydrofuran (250 mL) was cooled to 0° C. with stirring under N2 atmosphere. A solution of 4-(ethylthio)benzoic acid (25 g) in tetrahydrofuran (300 mL) was added at a rate so as to control H2 evolution. The reaction mixture was then allowed to warm to room temperature and stirred 15 hours. The mixture was cooled in ice and a solution of 15% aqueous sodium hydroxide solution was added, (6 mL) followed by water (21 mL). The mixture was stirred at ice temperature for 1 hour and for 2 hours at ambient temperature. The solution was decanted, diluted with diethyl ether and washed with saturated aqueous NaCl solution. The organic phase was dried over MgSO4, filtered through a celite pad and concentrated to give 4-(ethylthio)benzyl alcohol (20 g). This material was converted to the corresponding bromide as in Example 1 except that diethyl ether and hexane were used for the triturations rather than heptane and petroleum ether, respectively.

Aufarbeitung

  1. customThe starting 4-(ethylthio)benzyl alcohol was prepared
  2. temperatureto warm to room temperature
  3. stirringstirred 15 hours
  4. temperatureThe mixture was cooled in ice
  5. stirringThe mixture was stirred at ice temperature for 1 hour and for 2 hours at ambient temperature
  6. customThe solution was decanted
  7. additiondiluted with diethyl ether
  8. washwashed with saturated aqueous NaCl solution
  9. dry with materialThe organic phase was dried over MgSO4
  10. filtrationfiltered through a celite pad
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-04f09ebae8b4406697d7343bab8bb06c
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264451

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