Sodium Hydroxide → 1-(Ethoxycarbonyl)cyclobutane-1-carboxylic acid

To an ice-cooled solution of 100 ml of diethyl cyclobutane-1,1-dicarboxylate in 110 ml of methanol was added 290 ml of a 10% (w/w) sodium hydroxide aqueous solution over a period of 60 minutes while stirring. The solution was then stirred at room temperature for 18 hrs. The organic solvent methanol was then removed under reduced pressure. The aqueous layer was washed with chloroform and the aqueous layer was then acidified with conc. hydrochloric acid to a pH of 2.5. The aqueous layer was extracted with ethyl acetate, and the extract was washed with a sat. sodium chloride aqueous solution. The extract was dried and the solvent ethyl acetate was removed under reduced pressure. The residue was purified by vacuum distillation to yield 85 g of the titled compound as a colorless oil.

1. stirringThe solution was then stirred at room temperature for 18 hrs
2. customThe organic solvent methanol was then removed under reduced pressure
3. washThe aqueous layer was washed with chloroform
4. extractionThe aqueous layer was extracted with ethyl acetate
5. washthe extract was washed with a sat. sodium chloride aqueous solution
6. customThe extract was dried
7. customthe solvent ethyl acetate was removed under reduced pressure
8. distillationThe residue was purified by vacuum distillation

ORD record

ord-73525ec4baed4272869b225d8ca7cf6d

Source dataset

uspto-grants-1996_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05587386