Toluene → HCID 178495102, compound

Temperature

-10 °C

Commercially available methoxymethyltriphenylphosphonium chloride (127.5 g, 0.372 mol) was added to methyl t-butyl ether (1 l), followed by adding potassium t-butoxide (43.1 g, 0.384 mol) in argon atmosphere with stirring at -10° C. over 10 minutes, agitating the reaction solution at 0° C. for one hour, dropwise adding a solution of trans-4-(4-cyanophenyl)cyclohexylcarboaldehyde (V) obtained in Example 1, (i) (44.1 g, 0.207 mol) in methyl t-butyl ether (200 ml) at =10° C. over 15 minutes, agitating the resulting reaction solution at 0° C. for one hour, adding toluene (0.3 l) and water (0.3 l), subjecting the resulting toluene solution to four times washing with water (0.3 l) and separating, drying with anhydrous sodium sulfate, separating the drying agent, distilling off toluene, dissolving the resulting residue in ethyl acetate (100 ml) on heating, allowing the solution to stand still for one day, filtering off deposited crystals, concentrating the mother liquor, dissolving the concentrate in heptane, purifying according to silica gel column chromatography to obtain trans-1-(2-methoxy-1-ethenyl)-4-(cyanophenyl)cyclohexane (39.8 g, 0.165 mol), adding to the total quantity, tetrahydrofuran (500 ml) and 2N-hydrochloric acid (120 ml), heating the mixture under reflux with stirring for one hour, cooling the resulting reaction solution, adding toluene (300 ml) and water (1 l), washing subjecting the resulting toluene solution to three times washing with water (1 l) and separating, drying with anhydrous sodium sulfate, separating the drying agent and distilling off toluene to obtain trans-4-(4-cyanophenyl)cyclohexylacetaldehyde (VII) (35.4 g, 0.156 mol).

1. stirringagitating the reaction solution at 0° C. for one hour
2. stirringagitating
3. customthe resulting reaction solution at 0° C. for one hour
4. washwashing with water (0.3 l)
5. customseparating
6. dry with materialdrying with anhydrous sodium sulfate
7. customseparating the drying agent
8. distillationdistilling off toluene
9. dissolutiondissolving the resulting residue in ethyl acetate (100 ml)
10. temperatureon heating
11. waitto stand still for one day
12. filtrationfiltering off
13. concentrationconcentrating the mother liquor
14. dissolutiondissolving the
15. concentrationconcentrate in heptane
16. custompurifying

ORD record

ord-25110f3e6bed49cf8ff871ad1acc22f9

Source dataset

uspto-grants-1989_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04880562