Methanol → 3,3-Diphenylpentanedial

To a rapidly stirring solution of 14.24 g(0.04 mole) of diethyl 3,3-diphenylglutarate, prepared by the method of H. Ivanov and I. Anghelova, Comptes Rendus Acan. Bul. Sci., 18 (6), 529-32(1965), in 320ml of dry toluene at -78° C. under argon was added 61.12 ml (0.11 mole) of 1.86M DIBAL in toluene solution (Aldrich) over a period of 4 minutes. After 40 minutes, 40 ml of methanol was added over 4 minutes to the -78° C., stirring reaction mixture. After an additional 5 minutes of stirring, 80 ml of water was added over a 5 minute period while keeping the temperature of the reaction at -78° C. The reaction mixture was allowed to warm to room temperature and was stirred an addititional hour. The reaction mixture was filtered and the precipitated salts washed with 300 ml of warmed toluene (100° C.) and then 300 ml of boiling methylene chloride. The organic phase of the filtrate was separated, dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo giving a clear oil. The oil was used in the next step without further purification.

1. customreaction mixture
2. stirringAfter an additional 5 minutes of stirring
3. customthe temperature of the reaction at -78° C
4. stirringwas stirred an addititional hour
5. filtrationThe reaction mixture was filtered
6. washthe precipitated salts washed with 300 ml of warmed toluene (100° C.)
7. customThe organic phase of the filtrate was separated
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. customevaporated in vacuo
11. customgiving a clear oil
12. customThe oil was used in the next step without further purification

ORD record

ord-d25edaeab77540a2a3dd0b2205faf692

Source dataset

uspto-grants-1988_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04742068