Sodium Hydroxide → HCID 86661511, compound

Participants

Reaction Steps

An aqueous solution of NaOH (30 g in 60 mL of water) and tert-butyl bromoacetate (3.75 mL, 25.2 mmol) were added into a solution of 4-(hydroxymethyl)benzonitrile (3.0 g, 22.53 mmol) and tetrabutylammonium hydrogen sulfate (765 mg, 2.25 mmol) in toluene (60 mL). The reaction mixture was stirred at RT for 2 hours. The aqueous layer was removed and extracted twice with EtOAc. The organic layers were combined and washed with a saturated aqueous solution of NH4Cl and brine, and then dried (MgSO4) and concentrated to give the title compound as a colorless oil (4.37 g, 78%). HPLC (Method A) Rt 4.7 min (purity: 95.2%). 1H NMR (CDCl3, 300 MHz) δ 7.65 (d, J=8.4 Hz, 2H), 7.50 (d, J=8.4 Hz, 2H), 4.68 (s, 2H), 4.05 (s, 2H), 1.50 (s, 9H).

Provenance & Evidence