Hydrochloric Acid → HCID 53987327, compound

Temperature

-20 °C

To a solution of lithium diisiopropylamide (prepared from diisopropylamine (16.16 g, 0.16 mol and n-butyl lithium (1.6M in hexane, 100 ml, 0.016 mol) in THF (50 ml) at -78° C., was added a solution of 4-(4-methoxyphenyl)butanoic acid (13.80 g, 0.07 mol) in THF (100 ml) over 20 min. The solution was warmed to -20° C. and stirred for 2.5 h. Formaldehyde gas generated by warming paraformaldehyde (10 g) was then passed into the reaction mixture in a stream of nitrogen. After stirring for a further 2 h. at -20° C., hydrochloric acid (2N, 500 ml) was added and the reaction mixture was diluted with ethyl acetate (800 ml). After washing with water, the organic phase was extracted with sodium hydroxide solution (0.5N, 3×200 ml). The combined aqueous extracts were acidified with hydrochloric acid and extracted with ethyl acetate (3×200 ml), the combined organic phase (MgSO4) was dried and solvent removed at reduced pressure to give the product as a colourless solid.

1. stirringAfter stirring for a further 2 h. at -20° C.
2. washAfter washing with water
3. extractionthe organic phase was extracted with sodium hydroxide solution (0.5N, 3×200 ml)
4. extractionextracted with ethyl acetate (3×200 ml)
5. dry with materialthe combined organic phase (MgSO4) was dried
6. customsolvent removed at reduced pressure

ORD record

ord-5fc9290d0f0d4748bb107fcdbe5c0d35

Source dataset

uspto-grants-1986_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04579862