[4-(Phenoxymethyl)phenyl]acetic acid → HCID 66578029, compound

Participants

Reaction Steps

To a flask containing [4-(phenoxymethyl)phenyl]acetic acid (1.0 g, 4.13 mmol), in THF (20 mL) under external ice cooling was added a 1.0M sol of LiAlH4 in THF (8.3 mL, 8.3 mmol) (effervescence noted). The reaction mixture was stirred for three hours under ice cooling, then allowed to stir at room temperature for 48 hours. The reaction mixture was quenched with water (4.1 mL) and 1N NaOH (24 mL) then extracted into EtOAc (200 mL). The organic layer was washed with brine (150 mL). The organics were dried over Na2SO4, filtered and concentrated in vacuo to furnish 1.64 g of the title compound as a white solid (174%), containing aluminum salt impurities. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.90 (t, J=6.64 Hz, 2H) 3.88 (t, J=6.44 Hz, 2H) 5.05 (s, 2H) 6.93-7.02 (m, 3H) 7.22-7.36 (m, 4H) 7.40 (d, J=8.20 Hz, 2H).

Provenance & Evidence