Trifluoroacetic acid → (4-(Benzyloxy)phenyl)methanol

Participants

Reaction Steps

Phthalimidoacetaldehyde diethylacetate (5.3 g, 20 mmole) was dissolved in chloroform (100 mL) and a trifluoroacetic acid solution (50% aqueous, 80 mL) was added. The reaction mixture was stirred at room temperature for 12 hours. The chloroform layer was collected and dried over sodium sulfate. The filtrate was concentrated to give 3.75 g of the title compound (99% yield): TLC (Rf: 0.4; 40% EtOAc/Hexane), 1H NMR (DMSO-d6) δ 4.6 (s, 2 H, CH2), 7.8 (m, 4 H, Ar), 9.6 (s, 1 H, CHO). 13C NMR (DMSO-d6): δ 47.4 (CH2), 123.4 (Ar), 131.5 (Ar), 134.8 (Ar), 167.3 (CO), 196.8 (CHO).

Provenance & Evidence