Hydrochloric Acid → HCID 53987327, compound

Temperature

-20 °C

To a solution of lithium diisopropylamide (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-097f31c8678f4f648275c447cc73f2e8

Source dataset

uspto-grants-1988_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04758573