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

HRID 516432Notes

Reaction equation

[OH:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].Cl[CH2:19][C:20]([OH:22])=[O:21]>O>[C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1)(=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

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.

Workup

dissolutiondissolved
temperatureon reflux at 100° C. for 14 hours or overnight
temperatureAfter that time the solution was cooled down to room temperature
filtrationThe solution was filtered
dissolutionthe solid dissolved in acetone
filtrationThe acetone was filtered again
customthe acetone was evaporated to dryness
customThe product thus obtained
customAfter crystallization in chloroform

Sources & evidence

ORD record: ord-baa68c77732f45508560230ed9d7005a
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09110370B2

Reaction notes

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