Acetone → 2-(2,2-Dimethyl-1,3-dioxolan-4-yl)ethan-1-ol

Butane-1,2,4-triol (5.0 g, 47 mmol) was dissolved in MeOH (5 ml). Acetone (20 ml), MgSO4 (ca. 500 mg), and para-toluene sulfonic acid (p-TsOH) (catalytic amount) were added, and the mixture was allowed to stir for 5 days at room temperature. The mixture was filtered and the filtrate concentrated under reduced pressure. Methylene chloride (CH2Cl2) (20 ml) and water (20 ml) were added, the layers were separated, and the organic layer was washed with water (2×20 ml). The organic layer was dried (MgSO4), filtered, and the filtrate concentrated under reduced pressure to afford the product as a clear oil (5.15 g, 75%): 1H NMR (CDCl3) 4.23(dt, 1H, J=6.86 Hz), 4.04(t, 1H, J=6.06 Hz), 3.72(m, 2H), 3.54(t, 1H, J=7.72 Hz), 2.55(broad s, 1H), 1.77(dt, 2H, J=6.67 Hz), 1.34(d, 6H, J=15.68 Hz)ppm; IR (neat) 3420, 2980, 2930, 2870, 1710, 1455, 1370, 1250, 1215, 1155, 1055, 855, 732 cm-1.

1. filtrationThe mixture was filtered
2. concentrationthe filtrate concentrated under reduced pressure
3. additionMethylene chloride (CH2Cl2) (20 ml) and water (20 ml) were added
4. customthe layers were separated
5. washthe organic layer was washed with water (2×20 ml)
6. dry with materialThe organic layer was dried (MgSO4)
7. filtrationfiltered
8. concentrationthe filtrate concentrated under reduced pressure

ORD record

ord-b9fbfbd8f0104ce0b87e68404f11c7e7

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05233031