Water → HCID 178495106, compound

A suspension of 29.0 g of methoxymethyl-triphenylphosphonium chloride in 200 ml of t-butyl methyl ether was treated within 10 minutes with 9.7 g of potassium t-butylate while gassing with argon at -10° C. and the mixture was stirred for a further 1 hour. The mixture was then treated dropwise within 15 minutes at -10° C. with a solution of 12.0 g of trans-4-(p-cyanophenyl)cyclohexanecarboxaldehyde in 90 ml of t-butyl methyl ether and the resulting mixture was stirred for a further 1 hour at 0° C. The reaction mixture was subsequently poured into 150 ml of water and extracted three times with 150 ml of diethyl ether each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and concentrated. The resulting, viscous oil was dissolved in 20 ml of ethyl acetate and the clear solution was diluted with 300 ml of petroleum ether and left to stand for 10 minutes at -20° C. The precipitated triphenylphosphine oxide was subsequently filtered off and the filtrate was concentrated to dryness. Low-pressure chromatography (0.5 bar) of the residue (16.3 g) on silica gel with ethyl acetate/petroleum ether (vol. 5:95) gave 10.1 g (74%) of p-[trans-4-(2-methoxyvinyl)cyclohexyl]benzonitrile as colourless crystals; Rf-value (ethyl acetate/petroleum ether vol. 10:90) 0.32.

1. customwhile gassing with argon at -10° C.
2. stirringthe resulting mixture was stirred for a further 1 hour at 0° C
3. extractionextracted three times with 150 ml of diethyl ether each time
4. washThe organic phases were washed twice with 100 ml of water each time
5. dry with materialdried over magnesium sulphate
6. concentrationconcentrated
7. dissolutionThe resulting, viscous oil was dissolved in 20 ml of ethyl acetate
8. additionthe clear solution was diluted with 300 ml of petroleum ether
9. waitleft
10. waitto stand for 10 minutes at -20° C
11. filtrationThe precipitated triphenylphosphine oxide was subsequently filtered off
12. concentrationthe filtrate was concentrated to dryness

ORD record

ord-cc3fee89aab5414d8cba31aa3845eff5

Source dataset

uspto-grants-1986_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04621901