Resorcinol → 3-Chloro-1-(2,4-dihydroxyphenyl)propan-1-one

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Reaction Steps

To a stirred mixture of resorcinol (200 g, 1.82 mol) and 3-chloropropionic acid (200 g, 1.84 mol) was added trifluoromethane sulfonic acid (1 kg) in one portion. The solution was heated slowly over about 45 minutes to about 80° C. then cooled to room temperature over about 15 minutes and poured into chloroform (4.0 L). The organic portion was slowly poured into water (4.0 L) and the layers separated. The aqueous layer was extracted with chloroform (2×2.0 L). The combined organic layers were washed with brine, dried over sodium sulfate and filtered. Concentration in vacuo gave as an orange semi-solid (244.1 g) which was used crude in the next step. 1H-NMR (300 MHz, CDCl3): 12.56 (1H, s), 7.63 (1H, d, J=7.6), 6.376.46 (2H, m), 3.92 (2H, t, J=6.3), 3.41 (2H, t, J=6.3).

Provenance & Evidence