2,3-xylyl acetate synthesis
- Product Name:2,3-xylyl acetate
- CAS Number:22618-22-0
- Molecular formula:C10H12O2
- Molecular Weight:164.2
Yield:22618-22-0 99%
Reaction Conditions:
with triethylamine in dichloromethane at 0; for 0.166667 h;
Steps:
4.1. 2,3-Dimethylphenyl acetate (21)
To a solution of 2,3-dimethylphenol (50 g, 0.409 mol) in CH2Cl2(120 mL) at 0 °C was added Et3N (114 mL, 0.819 mol) followed by dropwise addition of Ac2O (58 mL, 0.6135 mol). After completion of the reaction in 10 min (monitored by TLC), ice-cold water was added, and the aqueous layer was extracted by using CH2Cl2. The organic layer was washed with brine solution, dried over Na2SO4, concentrated under reduced pressure. The compound was purifiedby flash column chromatography to get compound 21 as yellow color liquid (66.5 g). Yield: 99%; Rf 0.6 (10% EtOAc/hexanes); 1H NMR (400 MHz, CDCl3): δ 7.09 (dd, J=7.7, 7.3 Hz, 1H), 7.03 (d, J=7.3, 1H), 6.85 (d, J=7.7, 1H), 2.31 (s, 3H), 2.28 (s, 3H), 2.07 (s, 3H);13C{H} NMR (100 MHz, CDCl3): δ 169.5, 149.2, 138.5, 128.7, 127.5,126.1, 119.4, 20.8, 20.1, 12.4; IR (Neat): νmax 2931, 2858, 1753, 1463,1372,1253,1141,1060, 974, 829, 812, 776, 664; HRMS: (ESI-TOF) m/zcalcd for C10H13O2 (M+H+) 165.0928, found 165.0910.
References:
Mahesh, Gaddam;Raghavaiah, Jakka;Sudhakar, Gangarajula [Tetrahedron,2020,vol. 76,# 31-32,art. no. 131368]
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