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Terephthaldicarboxaldehyde (2.00 g, 14.91 mmol) was dissolved in tetrahydrofuran (25 ml) and cooled to 0° C. Octylmagnesium chloride (7.5 ml, 2.0M in THF, 15 mmol) was added dropwise. After 15 minutes, the reaction was quenched with 2N aqueous hydrochloric acid (50 ml) and diluted with ethyl acetate (50 ml). The organic layer was separated, washed with sat'd NaCl (50 ml), dried over magnesium sulfate and concentrated. Silica gel chromatography eluting with 91:9 v/v hexane/EtOAc gave 0.19 g (0.77 mmol, 5.1%) of the title compound: 1H NMR (500 MHz) δ 10.0 (s, 1H), 7.87 (d, J=8.0, 2H), 7.52 (d, J=8.3, 2H), 4.75-4.80 (m, 1H), 1.68-1.82 (m, 2H), 1.22-1.45 (m, 12H), 0.91 (t, J=7.0, 3H).

1. customthe reaction was quenched with 2N aqueous hydrochloric acid (50 ml)
2. additiondiluted with ethyl acetate (50 ml)
3. customThe organic layer was separated
4. washwashed with sat'd NaCl (50 ml)
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated
7. washSilica gel chromatography eluting with 91:9 v/v hexane/EtOAc