Chloroacetic Acid → 2-(4-Benzoylphenoxy)acetic acid

Participants

Reaction Conditions

Reaction Steps

20.5 grams (103.4 mmol) of 4-hydroxybenzophenone were suspended in water and dissolved adding 3 equivalents of NaOH. The solution was heated up to 90° C. A solution of 15 grams of chloroacetic acid (1.6 eq.) in 40 mL of water was added dropwise to the reactor for 30 minutes. After that, the reactor was put on reflux at 100° C. for 14 hours or overnight. After that time the solution was cooled down to room temperature and acidified to pH 1-3. A white precipitate appeared. The solution was filtered and the solid dissolved in acetone. The acetone was filtered again and the acetone was evaporated to dryness. The product thus obtained was significantly contaminated with starting material. After crystallization in chloroform, 12 grams of a >95% (4-benzoylphenoxy)acetic acid was obtained (45% yield). FIG. 5 is the UPLC analysis of the compound after crystallization in CHCl3 at 264 nm, using the PCP_FAST method in a C18 column. This compound was used as an endcapping agent.

Provenance & Evidence