Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, ethyl ester → gamma-Propanol

HRID 1165535

Reaktionsgleichung

Reaktionsgleichung von HRID 1165535
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([C:11]1[CH:12]=[C:13]([CH2:22][CH2:23][C:24](OCC)=[O:25])[CH:14]=[C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])[C:16]=1[OH:17])([CH3:10])[CH3:9]>C(OCC)C>[CH3:21][C:18]([C:15]1[CH:14]=[C:13]([CH2:22][CH2:23][CH2:24][OH:25])[CH:12]=[C:11]([C:8]([CH3:9])([CH3:7])[CH3:10])[C:16]=1[OH:17])([CH3:19])[CH3:20]

Komponenten

4

Edukt 2

HCID 64871Benzenepropanoic acid, 3,5-bis(1,1-dimethylethyl)-4-hydroxy-, ethyl esterHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 169766gamma-PropanolAusbeute 92,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a suspension lithium aluminum hydride (11.2 g) in diethyl ether (500 mL) is added over a period of 30 minutes ethyl 3-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]propionate (60.0 g) in diethyl ether (100 mL). The mixture is heated at reflux for 3 hours and then quenched by the sequential addition of water (11 mL), 10% aqueous sodium hydroxide (11 mL) and water (66 mL). The resulting suspension is washed with tetrahydrofuran and the filtrate is concentrated to give 48 g of 3-[3,5-bis(1,1-dimethylethyl)-4-hydroxy-phenyl]propanol. Trituration of the residue with heptane gave 46 g of light yellow crystals. The 1H NMR spectrum and field desorption mass spectrum are consistent with the above-specified product.

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 hours
  3. customquenched by the sequential addition of water (11 mL), 10% aqueous sodium hydroxide (11 mL) and water (66 mL)
  4. washThe resulting suspension is washed with tetrahydrofuran
  5. concentrationthe filtrate is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-3995a8fcdfb2460da415e3bbf07a5cfc
Quelldatensatz
uspto-grants-1990_03
Patentnummer
US04910286

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