Reaktion #1335277

Reaktionsgleichung

sulfuric acid

lithium aluminum hydride

trans-4-phenylcyclohexanecarboxylic acid methyl ester

Ethyl acetate

→

4-phenylcyclohexylmethanol

Ausbeute 92.2%

Lösungsmittel

tetrahydrofuran

THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthere was dropwise added a soltuion
2. 2
   Sonstigeobtained
3. 3
   Sonstigekept at 20° C.
4. 4
   workup.ADDITIONAfter completion of the addition
5. 5
   Sonstigefor 2 hours
6. 6
   Temperaturcooling
7. 7
   workup.DISSOLUTIONto dissolve inorganic matter
8. 8
   Sonstigeseparating the resulting organic layer and aqueous layer from one another,
9. 9
   workup.ADDITIONadding n-heptane (200 ml)
10. 10
    Extraktionto extract the organic layer
11. 11
    Waschenwashing the extract solution with water 500 ml),
12. 12
    Waschenthen washing with a 2% aqueous solution of Na2CO3
13. 13
    Waschenfurther washing with water until the aqueous layer
14. 14
    workup.DISTILLATIONdistilling off n-heptane and THF
15. 15
    Sonstigerecrystallizing the resulting solid as residue from n-heptane (20 ml)
16. 16
    Filtrationfiltering off crystals
17. 17
    Sonstigedrying

Vorschrift

Dry tetrahydrofuran (THF)(420 ml) was added to lithium aluminum hydride (11.1 g, 0.293 mol), and while the mixture was vigorously agitated, there was dropwise added a soltuion obtained by dissolving trans-4-phenylcyclohexanecarboxylic acid methyl ester (II) (64.0 g, 0.293 mol) in THF (70 ml), at a reaction temperature kept at 20° C. or lower. After completion of the addition, the reaction mixture was warmed up to 55° C., followed by reacting it for 2 hours and cooling. Ethyl acetate (12 ml) and water (100 ml) were then added, followed by adding a 1N aqueous solution of sulfuric acid (350 ml) to dissolve inorganic matter, separating the resulting organic layer and aqueous layer from one another, adding n-heptane (200 ml) to extract the organic layer, washing the extract solution with water 500 ml), then washing with a 2% aqueous solution of Na2CO3, further washing with water until the aqueous layer became neutral, distilling off n-heptane and THF, recrystallizing the resulting solid as residue from n-heptane (20 ml), filtering off crystals and drying to obtain 4-phenylcyclohexylmethanol (III) (51.4 g). M.P. 47.3°~48.5° C.

Quelle