4-Hydroxybenzaldehyde → 4-Formylphenyl 4'-methyl-[1,1'-biphenyl]-4-carboxylate

Participants

Reaction Steps

Prepared using General Procedure 2: To a stirred solution of 4′-methyl-[1,1′-biphenyl]-4-carboxylic acid (0.5 g, 2.35 mmol) in DCM (10 mL) was added DMF (3 drops) then oxalyl chloride (0.262 mL, 3.1 mmol) and left for 2 h. The reaction mixture was added to a solution of 4-hydroxybenzaldehyde (0.31 g, 2.6 mmol) and TEA (0.4 mL, 2.82 mmol) in DCM (10 mL) and stirred for 18 h. The reaction mixture was diluted with DCM (100 mL) and washed with NaHCO3 (100 mL). The organic layer was pre-absorbed onto silica gel and then purified by chromatography (EA/isohexanes) to afford 300 mg (40%) 4-formylphenyl 4′-methyl-[1,1′-biphenyl]-4-carboxylate INT-27 as a white solid. LCMS-ESI (m/z) calculated for C21H16O3: 316; no m/z observed, tR=4.25 min (Method 1).

Provenance & Evidence