Formaldehyde → 2-Butyl acrylic acid

Temperature

80 °C

Butylmalonic acid (25 g, 156 mmol) was dissolved in ethanol (250 ml) and 37% formaldehyde solution (15.45 ml, 156 mmol) was added followed by piperidine (47 ml, 624 mmol). The mixture was stirred overnight at 80° C. under a reflux condenser. The solvents were removed under reduced pressure and the residue was diluted with 1M hydrochloric acid and extracted with dichloromethane (3×30 ml). The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to afford the desired product as a yellow oil (25 g, with residual solvent). 1H-NMR: δ (CDCl3), 10.04 (1H, br s), 6.22 (1H, s), 5.57 (1H, d, J=1.3 Hz), 2.30 (2H, t, J=6.9 Hz), 1.38 (4H, m), and 0.91 (3H, t, J=7.2 Hz).

1. customThe solvents were removed under reduced pressure
2. additionthe residue was diluted with 1M hydrochloric acid
3. extractionextracted with dichloromethane (3×30 ml)
4. washThe combined organic extracts were washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. customevaporated

ORD record

ord-6de91ee069f34bb6a05ca5b7433c24af

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06787522B2