Hydrochloric Acid → 3-Propylbenzaldehyde

To a solution of 1-bromo-3-propylbenzene (16.6 g) in tetrahydrofuran (83 ml) cooled to −78° C. was added dropwise n-butyllithium (2.66M solution in n-hexane, 34 ml) over 9 minutes, and then the mixture was stirred for 1 hour. To this reaction solution was added dropwise N,N-dimethylformamide (7.7 ml) over 6 minutes, and the mixture was stirred for additional 20 minutes. To this reaction solution was added dropwise a 4M solution of hydrogen chloride in 1,4-dioxane (23 ml) over 5 minutes, and then the mixture was stirred after warming to room temperature. To this mixed solution was added water (83 ml), followed by a 6M aqueous solution of hydrochloric acid (12 ml), and then the mixture was extracted with n-hexane (80 ml). The resulting organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a crude product of the titled compound (14.0 g).

1. stirringthe mixture was stirred for additional 20 minutes
2. stirringthe mixture was stirred
3. extractionthe mixture was extracted with n-hexane (80 ml)
4. washThe resulting organic layer was washed with a saturated aqueous solution of sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure

ORD record

ord-84af22c7505842dcbca9c873322a2956

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846746B2