4-Aminophenol → 3-chloro-N-(4-hydroxyphenyl)propanamide

Participants

Reaction Conditions

Reaction Steps

The solution of 4-aminophenol (250 g, 2.29 mol, 1 equiv) in CH2Cl2(2L) and saturated NaHCO3 (2L) was stirred for 5 min at 25° C., then 3-chloropropanoyl chloride (314 g, 2.52 mol 1.1 equiv) was added dropwise and the reaction was stirred for an additional 3 h at 25° C. The solids were filtered and dried under high vacuum to afford 3-chloro-N-(4-hydroxyphenyl)propanamide was used to the next step directly. (250 g, crude). 1H NMR (400 MHz, DMSO) δ, 2.96-2.99 (m, 2 H), 4.06-4.10 (m, 2 H), 6.88-6.92 (m 2 H), 7.57-7.60 (m, 2 H), 9.38-9.39 (br, 1 H), 10.1 (br, 1 H).

Provenance & Evidence