Benzaldehyde, 4-(phenylmethoxy)- → HCID 54204380, compound

A solution of n-butyllithium in hexane (1.6 M, 20 ml) was added to a stirred suspension of finely powdered [3-(1-methoxy-1-methylethoxy)propyl] triphenylphosphonium bromide (14 g) in dry THF (100 ml) at 0°. The mixture was stirred at 0° for 30 min, treated with a solution of 4-(phenylmethoxy)benzaldehyde (5 g) in THF (25 ml), stirred at 0° for 2 h and filtered through silica. The filtercake was washed with ER, the combined filtrates evaporated in vacuo and the residual oil triturated with ER (50 ml) and filtered through silica. The filtrate was evaporated and the residue dissolved in THF-water-2 M hydrochloric acid (50:5:1, 56 ml) and kept at 23° for 20 min. The mixture was diluted with water (200 ml), extracted with ER (200 ml) and the extract was washed with water (100 ml), brine (50 ml) dried and evaporated to give a white solid which was stirred in hexane and filtered to give the title alcohol (5.2 g) m.p. 93°-95°.

1. stirringstirred at 0° for 2 h
2. filtrationfiltered through silica
3. washThe filtercake was washed with ER
4. customthe combined filtrates evaporated in vacuo
5. customthe residual oil triturated with ER (50 ml)
6. filtrationfiltered through silica
7. customThe filtrate was evaporated
8. dissolutionthe residue dissolved in THF-water-2 M hydrochloric acid (50:5:1, 56 ml)
9. waitkept at 23° for 20 min
10. additionThe mixture was diluted with water (200 ml)
11. extractionextracted with ER (200 ml)
12. washthe extract was washed with water (100 ml), brine (50 ml)
13. customdried
14. customevaporated
15. customto give a white solid which
16. filtrationfiltered

ORD record

ord-b4ce28d5b31d4831a552791d65f1dccc

Source dataset

uspto-grants-1991_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04990505