Benzene → 2-(4-Methoxyphenyl)-2-methylpropanal

Temperature

70 °C

Step A Under Argon, a mixture of NaOH (2.8 g, 70 mmol), tetrabutylammonium iodide (0.6 g, 1.6 mmol) in benzene (8 mL) and H2O (2.8 mL) was heated at 70° C. to form a homogeneous mixture. A mixture of 4-methoxybenzyl chloride (Aldrich) (10 g, 64 mmol) and isobutyraldehyde (5.76 g, 80 mmol) in benzene (22 mL) was added dropwise. The resulting reaction mixture was heated at 70° C. for 3 h. The mixture was cooled, extracted with ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:30) to give 2-(4-methoxy-phenyl)-2-methyl-propionaldehyde as a colorless oil (4.1 g, 33%).

1. customto form a homogeneous mixture
2. additionwas added dropwise
3. customThe resulting reaction mixture
4. temperaturewas heated at 70° C. for 3 h
5. temperatureThe mixture was cooled
6. extractionextracted with ethyl acetate
7. customThe organic layer was separated
8. extractionthe aqueous layer was extracted with ethyl acetate
9. concentrationconcentrated
10. customThe residue was purified by chromatography (EtOAc:hexanes=1:30)

ORD record

ord-c1abc39cca964d2f81b68421ce455d91

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354444B2