Lithium Hydroxide → HCID 9903533, compound

Participants

Reaction Steps

Lithium hydroxide (4.32 g, 0.18 mol, 3 eq) in water (80 mL) was added to a stirred solution of 2-phenylethyl 2-(2-phenylethoxy)-5-formylbenzoate (22.46 g, 0.06 mol, 1 eq) in a mixture of tetrahydrofuran (240 mL) and methanol (80 mL). The reaction mixture was stirred for 3 h, then concentrated in vacuo, and the residue diluted with water (100 mL), and washed with ethyl acetate (2×100 mL). The aqueous solution was acidified to pH 1 with concentrated HCl, extracted with ethyl acetate (2×100 mL), and the organic solution dried over sodium sulfate and evaporated. This gave a gummy solid, which was recrystallized from ethyl acetate and ether to give a pale yellow powder (8.87 g, 55% (2 steps)). RF (petroleum ether:ethyl acetate, 2:1) 0.35. 1H NMR (CDCl3) δ9.97 (s, 1H, O═C—H), 8.65 (d, 1H, J 2.3 Hz, ArH), 8.11 (dd, 1H, J 8.7 and 2.3 Hz, ArH), 7.18 (d, 1H, J 8.7 Hz, ArH), 4.58 (t, 2H, J 6.8 Hz, OCH2CH2Ph), 3.27 (t, 2H, J 6.8 Hz, OCH2CH2Ph).

Provenance & Evidence