Hydrochloric Acid → HCID 4067614, compound

Participants

Reaction Steps

A 250 mL flask fitted with a stir-bar was charged with ethyl 3-isobutoxyphenoxyacetate (9.11 g, 36.1 mmol, 71% purity) and EtOH (100 mL). To the resultant solution was added KOH (4.05 g, 72.2 mmol) in H2O (15 mL). The mixture stirred 30 min at rt. 1M HCl was then added until a pH of 2.5 was reached. The mixture was concentrated in vacuo to 75 mL. NaOH (4 g) was added, and the solution was washed with CH2Cl2 (3×50 mL). 3M HCl was then added until a pH of 3 was attained, and the mixture was extracted with EtOAc (75 mL). The organic phase was washed with brine (50 mL), filtered through phase separation paper, and concentrated in vacuo to give 5.2 g of 72 as an off-white solid (64% from 71). 1H NMR (60 MHz, CDCl3): δ 11.4 (s, 1H), 7.3-7.0 (m, 1H), 6.7-6.3 (m, 3H), 4.6 (s, 2H), 3.7 (d, 2H), 2.0 (nonet, 1H), 1.0 (d, 6H) ppm. HPLC analysis (5:10:85 H2O:A1:MeOH) showed a purity of 95% with a retention time of 3.5 min.

Provenance & Evidence