Water → 2-Methylbutyl 3-methylbut-2-enoate

At room temperature under nitrogen in a 500 ml flask, a mixture of 87.3 g of 3,3-dimethylacrylic acid (0.85 mol) and 134.7 g of DL-2-methyl-1-butanol (1.50 mol, 1.75 eq.) and 4.25 g of para-toluene suflonic acid monohydrate (0.024 mol, 0.026 eq.) was treated with 100 ml heptane and then heated at reflux at 90° C. for 14 hours while 15.4 ml (0.85 mol) of H2O was collected in a Dean-Stark trap. The result was an orange solution. The solution was extracted with MTBE/brine (2×350 ml/200 ml brine). The organic layers were washed with NaHCO3 (200 ml saturated solution), brine (200 ml), dried over MgSO4 and concentrated. 205 g of a orange liquid was recovered, which was purified by distillation over a 30 cm plate-column. 131.1 g of a colorless liquid was recovered (bp 58° C./3.5 torr (4.7 bar) 90.5% yield).

1. temperatureheated
2. customwas collected in a Dean-Stark trap
3. extractionThe solution was extracted with MTBE/brine (2×350 ml/200 ml brine)
4. washThe organic layers were washed with NaHCO3 (200 ml saturated solution), brine (200 ml)
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. custom205 g of a orange liquid was recovered
8. distillationwhich was purified by distillation over a 30 cm plate-column
9. custom131.1 g of a colorless liquid was recovered (bp 58° C./3.5 torr (4.7 bar) 90.5% yield)

ORD record

ord-5c8b57ba8fd846508367da31f1c7e75b

Source dataset

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07632964B2