Potassium Hydroxide → [4-(Diazo(phenyl)methyl)phenyl]methanol

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To a mixture of mercury (II) oxide (2.9 g, 13 mmol), sodium sulphate (2.2 g, 15 mmol) and sat potassium hydroxide in ethanol (4 ml) was added a solution of 4 (2.6 g, 11 mmol) in dry THF (20 ml). The mixture was stirred in the dark for 2 h. then filtered through a celite pad. Concentration of the filtrate in vacuo yielded 5 (2.4 g, 100%) as a dark red oil; δH (CDCl3) 4.69 (s, 2H, CH2OH), 7.29-7.31 (m, 4H, 3-, 3′-, 5-, 5′-H), 7.39-7.41 (m, 5H, 2-, 2′-, 4′-, 6-, 6′-H) ppm; δC (CDCl3) 64.8 (CH2OH), 125.1, 125.2 (3-, 3′-, 5-, 5′-C), 125.6 (4′-C), 127.9, 129.1 (2-, 2′-, 6-, 6′-C), 128.9, 129.4 (1-, 1′-C), 138.2 (4-C) ppm; νmax (thin film) 3346, 2872, 2038, 1511, 1493 cm−1; m/z (F14) 224 ([M]+, 100%); found (FT) 224.0949, C14H12N2O requires 224.0950.

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