Ethanol → HCID 46932893, compound

Participants

Reaction Steps

Cs2CO3 (27.0 g, 83 mmol) was added in portions to phenol (102) (14.5 g, 42 mmol) and MeI (8.0 mL, 125 mmol) in DMF (400 mL) at rt. After 3 h at 50° C., the reaction was decanted and washed with CH2Cl2 into an erlenmeyer which had been placed in an ice cooled bath. With stirring, 2M HCl was added slowly until acidic by pH paper. After warming to rt, the reaction was diluted with CH2Cl2 (800 mL) and H2O (400 mL). The layers are separated and the aqueous layer was reextracted with CH2Cl2 (300 mL). The organic layers were combined, washed with brine (400 mL), dried (Na2SO4) and concentrated under reduced pressure to provide a red sludge which could be tritrated with EtOH and filtered to afford (9.3 g, 66%) of (103) as a pink solid. Analytically pure material can be obtained at this point by column chromatography with 50% EtOH/hexane. (LH-63-5) 1H NMR (250 MHz, CDCl3) δ 7.84 (d, 1H, J=6.0Hz), 7.42−7.31 (complex, 5H), 7.20−7.07 (complex, 2 H), 6.63 (s, 1H), 6.37 (s, 1H), 5.08 (s, 2H), 3.92 (s, 3H), 3.88 (s, 3H); 13C NMR (62.5 MHz) δ 175.2, 163.8, 161.7, 159.4, 147.8, 144.5, 135.6, 128.6, 128.3, 127.5, 123.9, 123.1, 117.5, 114.3, 106.1, 95.9, 93.6, 70.4, 56.3, 56.2; mass spectrum (CI) m/z+1 363.1242 [C22H19O5 (M+1) requires 363.1232] 363 (base), 339.

Provenance & Evidence