Phenylacetic Acid → HCID 58110045, compound

Participants

Reaction Steps

Step AAO (1): 2-Phenylacetic acid (2.19 g, 16.1 mmol) was deprotonated with NaHMDS 2.0 M in THF (18.1 mL, 36.2 mmol) and reacted with 1-chloro-4-iodobutane (3.87 g, 17.7 mmol) using a procedure analogous to Step AC (1) to afford 6-chloro-2-phenylhexanoic acid (3.57 g, quantitative yield) as a pale yellow oil. LC-MS (M−H)− 225.1. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.25-7.39 (5 H, m), 3.58 (1 H, t, J=7.6 Hz), 3.52 (2 H, t, J=6.7 Hz), 2.12 (1 H, dddd, J=13.4, 10.5, 7.8, 5.5 Hz), 1.73-1.90 (3 H, m), 1.34-1.54 (2 H, m).

Provenance & Evidence