Reaction #1563923

Reaction equation

1-(2,2-dimethoxyethoxy)-4-fluorobenzene

trifluoroacetic acid

→

title compound

2-(4-fluorophenoxy)acetaldehyde

Solvents

chloroform

Conditions

Workup

1. 1
   Temperatureheat to 65° C.
2. 2
   workup.STIRRINGstir for 4 h
3. 3
   ConcentrationConcentrate the mixture under reduced pressure

Procedure

Dissolve 1-(2,2-dimethoxyethoxy)-4-fluorobenzene (1.00 g, 4.99 mmol) in chloroform (5.0 mL) and treat the mixture with trifluoroacetic acid (0.755 mL, 9.99 mmol). Stir the mixture at room temperature for two days, then heat to 65° C. and stir for 4 h. Concentrate the mixture under reduced pressure to furnish the title compound as a colorless oil in ca. 70% purity, as indicated by 1H NMR analysis (550 mg, 71% uncorrected yield). 1H NMR (400 MHz, CDCl3): δ 9.85 (t, J=0.5 Hz, 1H), 7.00 (dd, J=8.9, 8.5 Hz, 2H), 6.85 (dd, J=9.5, 4.3 Hz, 2H), 4.55 (br s, 2H).

Source