4-Nitrobenzaldehyde → 1,2-Bis(4-nitrophenyl)ethanone

A solution of KOH (7.56 g, 0.13 mol) in MeOH (75 ml) was added to the phosphonate ester 33 (62.1 g, 0.13 mol) in THF (400 ml) at -78° C. for 0.5 hour and p-nitrobenzaldehyde (20.3 g, 0.13 mol) in 200 ml of THF was added over 0.5 hour. The reaction was warmed to room temperature and stirred an additional 2 hours. THF was removed under reduced pressure. The residue was taken up in EtOAc and washed twice with 5% aqueous NaHCO3 and once with brine. The ethyl acetate was removed under reduced pressure. The dark red enemine was dissolved in CH3OH (600 ml) and concentrated HCl (0.2 ml) was added. The solution was stirred for 1 hour at room temperature and diluted with H2O (500 ml). The solid was filtered, washed with ether and dried to afford 34 (35.6 g, 82.0%), m.p. 131°-133° C.

1. customTHF was removed under reduced pressure
2. washwashed twice with 5% aqueous NaHCO3 and once with brine
3. customThe ethyl acetate was removed under reduced pressure
4. dissolutionThe dark red enemine was dissolved in CH3OH (600 ml)
5. additionconcentrated HCl (0.2 ml) was added
6. stirringThe solution was stirred for 1 hour at room temperature
7. additiondiluted with H2O (500 ml)
8. filtrationThe solid was filtered
9. washwashed with ether
10. customdried

ORDレコード

ord-ef995545ee344040b997866794cd2f2f

出典データセット

uspto-grants-1992_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05098918