Hydrogen Peroxide → 2-(1-hydroxycyclopentyl)acetic acid

This product is oxidized by the Baeyer-Villiger procedure. (1R)-Norbornanone (81, 18 mmol) is stirred with sodium acetate (9 g, water-free), hydrogen peroxide (27 ml, 30%), and acetic acid (9 ml) at 5° C. in the dark for 40 hours. The reaction is quenched by the addition of sodium sulfite (50 ml of a 10% aqueous solution) at 0° C. The product is extracted twice with EtOAc (600 ml). The extract is washed with the sodium sulfite solution, then with sodium bicarbonate solution (50 ml, saturated), then with sodium chloride solution (saturated), dried and evaporated. The product is chromatographed on silica (380 g, ether) to yield the lacton of 3 hydroxycyclopentane-1-acetic acid (82, 12 mmol, 67%).

1. customThe reaction is quenched by the addition of sodium sulfite (50 ml of a 10% aqueous solution) at 0° C
2. extractionThe product is extracted twice with EtOAc (600 ml)
3. washThe extract is washed with the sodium sulfite solution
4. dry with materialwith sodium bicarbonate solution (50 ml, saturated), then with sodium chloride solution (saturated), dried
5. customevaporated
6. customThe product is chromatographed on silica (380 g, ether)

ORD record

ord-7c2649edde5f475783fa29eb77f4d231

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05216141