Trifluoroacetic acid → 2-(4-Fluorophenoxy)acetaldehyde

HRID 1854227Notes

Reaction equation

HRID 1854227 reaction equation
C[O:2][CH:3](OC)[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[F:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]=[O:2])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59346670HCID 59346670, compound

Product 1

HCID 110518692-(4-Fluorophenoxy)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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).

Workup

  1. temperatureheat to 65° C.
  2. stirringstir for 4 h
  3. concentrationConcentrate the mixture under reduced pressure

Sources & evidence

ORD record
ord-7c439639c76d46f78ba074c77ec7ced0
Source dataset
uspto-grants-2015_02
Patent number
US08962659B2

Reaction notes

Loading…