Acetaldehyde → 3-Methyl-1(3H)-isobenzofuranone

Temperature

-78 °C

To a solution of 2-bromobenzoic acid (0.50 g, 2.49 mmol) in THF (12.0 ml) cooled at −78° C. was added 2.5M n-BuLi in hexane (2.0 ml). After stirring for 25 minutes, a solution of acetaldehyde (0.142 g, 3.23 mmol) in THF (0.3 ml) was added. The reaction was allowed to warm to room temperature after 8 minutes at −78° C., and then quenched into 10% HCl aqueous solution (30 ml). The acidic solution was rapidly stirred for 1.5 hours, and then extracted with EtOAc. The combined organic layers were washed with saturated NaHCO3 aqueous solution, brine, dried with anhydrous Na2SO4, and rotary evaporated to an oily residue. Gradient chromatography of the oil residue through a silica gel column with 20% to 30% EtOAc in hexane afforded 3-methyl-2-benzofuran-1(3 H)-one as a clear oil (130 mg, 35%).

1. customquenched into 10% HCl aqueous solution (30 ml)
2. stirringThe acidic solution was rapidly stirred for 1.5 hours
3. extractionextracted with EtOAc
4. washThe combined organic layers were washed with saturated NaHCO3 aqueous solution, brine
5. dry with materialdried with anhydrous Na2SO4
6. customrotary evaporated to an oily residue

ORD record

ord-afb47e42fae549839f4474ece4107bb4

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060844B2