| Identification | Back Directory | [Name]
2-(2-Chloro ethoxy) Ethyl acetate | [CAS]
14258-40-3 | [Synonyms]
NSC 72730
ethyl 2-(2-chloroethoxy)acetate
2-(2-Chloroethoxy)ethanol acetate
Ethanol,2-(2-chloroethoxy)-, 1-acetate | [Molecular Formula]
C6H11ClO3 | [MDL Number]
MFCD06252168 | [MOL File]
14258-40-3.mol | [Molecular Weight]
166.6 |
| Chemical Properties | Back Directory | [Boiling point ]
223℃ | [density ]
1.119 | [Fp ]
92℃ | [storage temp. ]
Inert atmosphere,2-8°C | [InChI]
InChI=1S/C6H11ClO3/c1-6(8)10-5-4-9-3-2-7/h2-5H2,1H3 | [InChIKey]
ZUZWLUYOVJTJAG-UHFFFAOYSA-N | [SMILES]
C(OC(=O)C)COCCCl |
| Hazard Information | Back Directory | [Synthesis]
To a stirred solution of 2-(2-chloroethoxy)ethan-1-ol (20.0 g, 160 mmol) in anhydrous dichloromethane (50 mL) was added triethylamine (Et3N, 33.4 mL, 176 mmol) and stirred at room temperature for 10 minutes. The reaction mixture was cooled to 0 °C and a dichloromethane (50 mL) solution of acetic anhydride (16.6 mL, 240 mmol) was added dropwise. Subsequently, the reaction mixture was warmed to room temperature and stirring was continued for 3 hours. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography using 40% ethyl acetate/hexane as eluent to give 2-chloroethoxyethyl acetate. Yield: 17.5 g, 88%; 1H NMR (400 MHz, DMSO-d6) δ 4.12 (t, J = 4.5 Hz, 2H), 3.75-3.60 (m, 6H), 2.02 (s, 3H). | [References]
[1] Journal of Organic Chemistry, 2011, vol. 76, # 7, p. 2010 - 2028
[2] European Journal of Organic Chemistry, 2009, # 7, p. 1082 - 1092
[3] Patent: WO2018/98206, 2018, A1. Location in patent: Paragraph 0927
[4] ChemPlusChem, 2017, vol. 82, # 3, p. 423 - 432
[5] Patent: US2017/253569, 2017, A1. Location in patent: Paragraph 0990-0991 |
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