Water → HCID 178444453, compound

Temperature

0 °C

A mixture of 54 g of (4-butyloxyphenyl)methyl-triphenylphosphonium bromide and 450 ml of absolute t-butyl methyl ether was treated with 12 g of solid potassium t-butylate at 0° C. and while gassing with nitrogen. After completion of the addition the reaction mixture was stirred at 0° C. for a further 15 minutes (whereby a deep orange coloration resulted) and then treated within 30 minutes at 0° C. with a solution of 15 g of 3-(trans-4-pentylcyclohexyl)propionaldehyde in 150 ml of absolute t-butyl methyl ether. Subsequently, the reaction mixture was stirred at room temperature overnight and then poured into 1000 ml of water and extracted three times with 200 ml of diethyl ether each time. The organic phases were washed twice with 500 ml of concentrated sodium chloride solution each time, dried over magnesium sulfate, filtered and subsequently concentrated. Chromatography of the residue on silica gel with hexane/toluene (vol. 4:1) gave 21 g of 1-butyloxy-4-[4-(trans-4 -pentylcyclohexyl)-1-butenyl]benzene (cis/trans mixture). Recrystallization from ethanol gave pure trans isomer with m.p. (C-SB) 46° C., SB --SA 74° C., SA --N 76° C. and cl.p. (N--I) 91° C.

1. additionAfter completion of the addition the reaction mixture
2. customresulted) and
3. stirringSubsequently, the reaction mixture was stirred at room temperature overnight
4. extractionextracted three times with 200 ml of diethyl ether each time
5. washThe organic phases were washed twice with 500 ml of concentrated sodium chloride solution each time
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationsubsequently concentrated

ORD record

ord-9596eb0180bf42f5b94e1d38c03af358

Source dataset

uspto-grants-1994_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05346647