Acetic Anhydride → alpha-Nitro-beta-ethoxyacrylic acid methylester

HRID 616263

Reaction equation

HRID 616263 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH2:4][N+:5]([O-:7])=[O:6].[CH:9](OCC)(OCC)[O:10][CH2:11][CH3:12].C(OC(=O)C)(=O)C>>[CH3:1][O:2][C:3](=[O:8])[C:4]([N+:5]([O-:7])=[O:6])=[CH:9][O:10][CH2:11][CH3:12]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 17206Methyl 2-nitroacetateHCID 31214Ethyl orthoformate

Product 1

HCID 53395203alpha-Nitro-beta-ethoxyacrylic acid methylesterYield 84.5%

Procedure

A 12-l. three-necked flask, equippedewith a thermometer, mechanical stirrer and a reflux condenser was charged under an atmosphere of nitrogen with 746 g (6.26 moles) of nitroacetic acid methylester, 1392 g (9.4 moles) of triethyl orthoformate and 1.92 l of acetic anhydride. The mixture was stirred and heated at reflux for 23 hours. The volatile components were distilled off first at atmospheric pressure (pot temperature up to 100° C, then at aspirator; vacuum and finally at 0.17 mmHg, (pot temperature up to 70°), leaving 926 g (84%) of crude alpha-nitro-beta-ethoxyacrylic acid methylester as an orange oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 23 hours
  3. distillationThe volatile components were distilled off first at atmospheric pressure (pot temperature up to 100° C

Sources & evidence

ORD record
ord-f7396bc9f65f41088d8d53343f8429c9
Source dataset
uspto-grants-1978_02
Patent number
US04073795

Linked notes

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