Diethyl Ether → Acetic acid 2-chloromethoxy-ethyl ester

HRID 266232

Reaction equation

HRID 266232 reaction equation
[C:1]([Cl:4])(=[O:3])C.[O:5]1[CH2:9][CH2:8][O:7][CH2:6]1.[CH3:10]COCC>[Cl-].[Zn+2].[Cl-]>[C:6]([O:7][CH2:8][CH2:9][O:3][CH2:1][Cl:4])(=[O:5])[CH3:10]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 6367Acetyl chlorideHCID 125861,3-Dioxolane

Product 1

HCID 10034810Acetic acid 2-chloromethoxy-ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Procedure

A solution of acetyl chloride (43.2 g, 550 mmol) in 100 mL of dry ether was added dropwise over 1 hour to a solution of 1,3 dioxolane (37.1 g, 500 mmol) in 300 mL of ether containing a few crystals of zinc (II) chloride at room temperature under nitrogen. The reaction mixture was stirred at room temperature for an additional 2 hours and then concentrated in vacuo. The product was purified by distillation (0.6 mmHg, 56°-58° C.) to provide 67.9 g (89%) of 1-acetoxy-2-(chloromethoxy)ethane as a clear colorless oil. cf: Foye, W. O.; Kaufmann, J. M.; Kim, Y. H. J. Heterocyclic Chem. 1987, 19, 497.

Workup

  1. concentrationconcentrated in vacuo
  2. distillationThe product was purified by distillation (0.6 mmHg, 56°-58° C.)

Sources & evidence

ORD record
ord-41d59d99c5ab4efb98f1d86b1a42ad72
Source dataset
uspto-grants-1997_07
Patent number
US05650510

Linked notes

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