4-Acetylphenylboronic acid → Ethyl (4-acetylphenyl)acetate
Reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CCCCCC.[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20]>>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:20][C:19]([O:22][CH2:23][CH3:24])=[O:21])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]Participants
Procedure
Ethyl 4-acetylphenylacetate was prepared by the general experimental method from 4-acetylphenylboronic acid (164 mg, 1.00 mmol). After workup by column chromatography (hexane/ethyl acetate, 5:1), ethyl 4-acetylphenylacetate is obtained as a colourless solid in a yield of 60% of theory. 1H NMR (400 MHz, CDCl3): δ=7.90 (d, J=8.2 Hz, 2H), 7.37 (d, J=8.5 Hz, 2H), 4.11-4.17 (m, 2H), 3.66 (s, 2H), 2.58 (s, 3H), 1.20-1.27 (m, 3H) ppm; 13C NMR (151 MHz, CDCl3): δ=197.7, 170.8, 139.5, 136.0, 129.6, 128.6, 61.1, 41.3, 26.6, 14.2 ppm; MS (70 eV), m/z (%): 192 (100), 164 (16), 134 (14), 105 (19), 89 (11); IR (KBr): ν=2981 (w), 1735 (s), 1682 (m), 1274 (m), 1178 (m) cm−1; elemental analysis: (theor): C=69.89, H=6.84, (exp): C=69.95, H=6.99. Melting point: 55-56° C.
Sources & evidence
- ORD record
- ord-7522a678da97497f96b3701325fb2724
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507688B2
Reaction notes
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