Triethylamine → 4-Benzoylphenyl methacrylate

HRID 45411

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.[C:16](Cl)(=[O:20])[C:17]([CH3:19])=[CH2:18].C(N(CC)CC)C>C(Cl)Cl>[C:16]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6](=[O:7])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:14][CH:15]=1)(=[O:20])[C:17]([CH3:19])=[CH2:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 100 mL round-bottomed flask equipped with a magnetic stirrer bar and an addition funnel was added 4-hydroxybenzophenone (1 g, 5.04 mmol) and CH2Cl2 (35 mL). The mixture was cooled to 0° C. and methacryloyl chloride (0.39 mL, 4.04 mmol) was added in one portion. After 30 minutes, triethylamine (0.7 mL, 5.04 mmol) dissolved in CH2Cl2 (10 mL) was added dropwise over 30 minutes. The reaction mixture was allowed to stir for a further 1 hour at 0° C. and then at room temperature for 3 hours. After this time, the organic mixture was washed with 0.1% NaOH (3×100 mL) and water (5×100 mL). The combined organic layers were dried over MgSO4 and then concentrated in vacuo to afford a crude product. The crude product was purified by column chromatography (100% CH2Cl2) to provide the compound as a white solid (yield=75%, 1 g).

Workup

customTo a 100 mL round-bottomed flask equipped with a magnetic stirrer bar and an addition funnel
additionwas added dropwise over 30 minutes
waitat room temperature for 3 hours
washAfter this time, the organic mixture was washed with 0.1% NaOH (3×100 mL) and water (5×100 mL)
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated in vacuo
customto afford a crude product
customThe crude product was purified by column chromatography (100% CH2Cl2)

Sources & evidence

ORD record: ord-e1aa9878c70e4e53b3a4696026417540
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541498B2

Linked notes

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