Water → HCID 90101567, compound

Participants

Reaction Conditions

Reaction Steps

Polyphosphoric acid (PPA) (250 g) was charged to a reaction vessel and warmed to 50° C. (bath temperature) with mechanical stirring. 2-Phenylacetic acid (30.6 g, 0.225 mol) was added to PPA followed by 2-phenoxyethyl pivalate (50 g, 0.225 mol). After 3 hours TLC and HPLC indicated full conversion and water (1000 ml) was added. The mixture was stirred at room temperature for 2 h. The precipitated product was filtered and washed with water (300 ml). After drying in vacuo the crude product (65 g) was re-crystallized with hexane/i-PrOH 1:1 yielding the title compound as slightly yellow solid (51.49 g, 0.151 mol, 67%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 8.02 (2H, d, J=9.2 Hz, ArH), 7.32-7.22 (5H, m, ArH), 7.07 (2H, d, J=8.8 Hz, ArH), 4.37 (2H, m, CH2CH2OPiv), 4.31 (2H, s, ArCH2CO), 4.3 (2H, m, ArOCH2CH2), 1.12 (9H, s, 3×Me). 13C-NMR (100 MHz, DMSO-d6) δ (ppm): 196.4, 177.7, 162.6, 135.8, 131.2, 129.9, 129.8, 128.7, 126.8, 114.8, 66.5, 62.7, 44.8, 38.6, 27.2.

Provenance & Evidence