ChemicalBook CAS DataBase List 2,3-xylyl acetate

2,3-xylyl acetate synthesis

9synthesis methods

Product Name:2,3-xylyl acetate
CAS Number:22618-22-0
Molecular formula:C10H12O2
Molecular Weight:164.2

526-75-0 Synthesis

526-75-0
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22618-22-0
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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%; R_f 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): ν_max 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.