Acetic Anhydride → Ethyl 2-(2-chloro-4-iodo-benzoyl)-3-ethoxy-acrylate

HRID 963400Notes

Reaction equation

HRID 963400 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH:17](OCC)(OCC)[O:18][CH2:19][CH3:20].C(OC(=O)C)(=O)C>>[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:10](=[CH:17][O:18][CH2:19][CH3:20])[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:16]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 19081721Ethyl 3-(2-chloro-4-iodo-phenyl)-3-oxo-propionate

Product 1

HCID 53916769Ethyl 2-(2-chloro-4-iodo-benzoyl)-3-ethoxy-acrylateYield 90%

Procedure

md) 53.7 g of ethyl 3-(2-chloro-4-iodo-phenyl)-3-oxo-propionate are heated to boiling under reflux for 4 hrs. with 40 g of triethyl orthoformate and 46.1 g of acetic anhydride. The volatile constituents are distilled off in a water-jet vacuum and finally in a high vacuum. 55.9 g (90%) of ethyl 2-(2-chloro-4-iodo-benzoyl)-3-ethoxy-acrylate are obtained as a yellowish oil. Mass spectrum: peaks inter alia at 408 (M+, 4%), 373 (67%), 342 (14%), 335 (100%).

Workup

  1. temperatureunder reflux for 4 hrs
  2. distillationThe volatile constituents are distilled off in a water-jet vacuum and finally in a high vacuum

Sources & evidence

ORD record
ord-f30372f5d3ff4c65a6638ec5f0321b17
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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