Water → 2-Chloro-4-cyclopropylbenzaldehyde

Temperature

-10 °C

To a solution of 7.01 ml Red-Al 13.5 M (24.54 mmol) in toluene was added at 0° C. a solution of 3.0 ml 1-methylpiperazine (26.89 mmol) in 16 ml toluene over 30 min. The resulting solution was then added dropwise over 40 min to 1.1 g of 2-chloro-4-cyclopropyl-benzoic acid methyl ester (5.2 mmol) in 32 ml toluene between −5° C. and 0° C. After stirring for 30 min at this temperature, the reaction mixture was cooled to −10° C. and treated dropwise with 30 ml water. The mixture was then filtered, diluted with ethylacetate, washed with 1N—HCl, brine, dried over magnesium sulfate, filtered again and concentrated in vacuo, leading to 0.98 g of 2-chloro-4-cyclopropyl-benzaldehyde as a brown oil (100%). MS (+cEI): 180.1 (M).

1. filtrationThe mixture was then filtered
2. additiondiluted with ethylacetate
3. washwashed with 1N—HCl, brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered again
6. concentrationconcentrated in vacuo

ORD record

ord-6cfb2e477f644487a0f4516c356334c8

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678818B2