Hydrochloric Acid → 3-tert-Butyl-5-(chloromethyl)-2-hydroxybenzaldehyde

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Reaction Steps

A mixture of 3-tert-butylsalicylaldehyde (7)(3.56 g, 20 mmol) and paraformaldehyde (1.20 g, 40 mmol) was stirred with concentrated HCl (15 mL) for 14 days, although with the first drops of concentrated HCl, the emulsion became red. The mixture was then treated with a saturated solution of Na2CO3 until neutralisation. The mixture was extracted with EtOAc (3×30 mL). Organic layers were dried over MgSO4 and the volatiles were evaporated under low pressure to give a beige solid which did not require further purification. Yield: 97%. Beige to red solid. 1H-NMR δH (CDCl3, 300 MHz): 1.43 (9H, s, 3×CH3), 4.59 (2H, s, CH2), 7.43, 7.52 (2H, 2d, J=2.1 Hz, 2×HAr), 9.87 (1H, s, CHO), 11.86 (1H, s, OH).

Provenance & Evidence