1,2,3,4-Tetrahydro-2-naphthoic acid → (1,2,3,4-Tetrahydronaphthalen-2-yl)methanol

HRID 394564

Reaktionsgleichung

Reaktionsgleichung von HRID 394564
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11](O)=[O:12].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:12][CH2:11][CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:1]1

Komponenten

4

Edukt 2

HCID 1013701,2,3,4-Tetrahydro-2-naphthoic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 245056(1,2,3,4-Tetrahydronaphthalen-2-yl)methanolAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1,2,3,4-tetrahydro-2-naphthoic acid (2.50 g, 14.2 mmol) in 100 ml THF was treated with LiAlH4 (681 mg, 17.04 mmol) and the reaction mixture was heated at reflux for 5 hours. The suspension was cooled to 0° C. and quenched by addition of solid Na2SO4▪10H2O. The mixture was stirred at room temperature for 4 hours. The solid was removed by filtration. Concentration of filtrate in vacuo gave a yellowish oil (2.28 g, 98.8%); 1H NMR (CDCl3, 300 MHz) δ1.43 (m, 1H), 2.00 (m, 2H) 2.51 (dd, J1=16.5 Hz, J2=10.8 Hz, 1H), 2.85 (m, 3H), 3.65 (dd, J1=6.3 Hz, J2=1.2 Hz, 2H), 7.09 (s, 4H).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 5 hours
  3. customquenched by addition of solid Na2SO4▪10H2O
  4. customThe solid was removed by filtration

Quellen und Nachweise

ORD-Eintrag
ord-96acdea526824374baa6cd1db350abc5
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602888B2

Verknüpfte Notizen

Wird geladen…