Toluene → HCID 178448053, compound

Commerically available methoxymethyltriphenylphosphonium chloride (102.7 g, 0.300 mol) was added to methyl t-butyl ether (1 l), followed by adding potassium t-butoxide (33.7g, 0.300 mol) in argon atmosphere at -10° C. in 10 minutes with stirring, agitating the reaction mixture at 0° C. for one hour, dropwise adding a solution of trans-4-(trans-4-propylcyclohexyl)cyclohexylacetaldehyde (50 g, 0.200 mol) prepared in item (ii) of Example 7, in methyl t-butyl ether (200 ml), at -10° C. in 15 minutes, agitating the reaction mixture at 0° C. for one hour, adding toluene (0.3 l) and water (0.3 l), four times washing the toluene solution with water (0.3 l) in a washing and separating manner, drying the organic layer over anhydrous sodium sulfate, separating the drying agent, distilling off toluene, dissolving the residue in ethyl acetate (100 ml) on heating, allowing the solution to stand still at room temperature for one day, filtering off deposited crystals, concentrating the mother liquor, dissolving the concentrate in heptane and purifying the solution with silica gel column chromatography to obtain trans-1-(3-methoxy-2-propenyl)-4-(trans-4-propylcyclohexyl)cyclohexane (42.6 g, 0.153 mol), adding to the total quantity thereof, tetrahydrofuran (330 ml) and 2N-hydrochloric acid (90 ml), heating the mixture under reflux with stirring for one hour, cooling the reaction mixture, adding toluene (300 ml) and water (1 l), three times washing the toluene solution with water (1 l) in a washing and separating manner, drying the organic layer over anhydrous sodium sulfate, separating the drying agent, distilling off toluene and drying the residue under reduced pressure to obtain 3-[trans-4-propylcyclohexyl)cyclohexyl]-1-propanal (35.6 g, 0.135 mol).

1. stirringagitating the reaction mixture at 0° C. for one hour
2. stirringagitating the reaction mixture at 0° C. for one hour
3. washwashing the toluene solution with water (0.3 l) in a washing and
4. customseparating manner
5. dry with materialdrying the organic layer over anhydrous sodium sulfate
6. customseparating the drying agent
7. distillationdistilling off toluene
8. dissolutiondissolving the residue in ethyl acetate (100 ml)
9. temperatureon heating
10. filtrationfiltering off
11. concentrationconcentrating the mother liquor
12. dissolutiondissolving the
13. concentrationconcentrate in heptane
14. custompurifying the solution with silica gel column chromatography

ORD record

ord-98f9bb7bf6cb41c08eb324e4f7220294

Source dataset

uspto-grants-1989_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04877548