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(2-TERT-BUTOXY)BENZALDEHYDE synthesis

4synthesis methods
-

Yield: 70%

Reaction Conditions:

with manganese dioxide in hexane;dichloromethane;ethyl acetate

Steps:

12 2-tert-butoxybenzaldehyde [8]
Example 12 2-tert-butoxybenzaldehyde [8] To a stirred solution of 7 (3.8 g, 21 mmol) in 250 mL CH2Cl2, MnO2 (11 g, 126 mmol) was added. The reaction mixture was stirred overnight, filtered on Celite and the solvent was distilled under reduced pressure. The crude product was purified by a silica gel column with 17% EtOAc/83% Hexane as eluents. The product was isolated as pale yellow oil (70% yield). 1H NMR (CDCl3) δ 7.286 (dd, 1H, Ar), 7.195 (ddd, 1H, Ar), 7.063 (d, 1H, Ar), 7.003 (ddd, 1H, Ar), 4.669 (s, 2H, -CH2-), 1.447 (s, 9H, -C(CH3)3). Mass Spec.=203.09 (M+H)++Na+.

References:

President and Fellows of Harvard College US2012/269724, 2012, A1