Ethylene carbonate → HCID 13259764, compound

HRID 544259Notes

Reaction equation

HRID 544259 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11].C1(=O)O[CH2:28][CH2:27][O:26]1>[I-].C([N+](CC)(CC)CC)C.CCOCC>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([O:12][CH2:28][CH2:27][OH:26])=[O:11]

Participants

5

Reactant 2

HCID 7303Ethylene carbonateHCID 44073Acifluorfen

Product 1

HCID 13259764HCID 13259764, compound

Reagents, catalysts & solvents 2

HCID 6225Tetraethylammonium IodideCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid (7.24 g, 0.02 mole), ethylene carbonate (2.0 g, 0.023 mole) and tetraethylammonium iodide (1.0 g) was heated in an oil bath at 105°-110° C. for 10 hrs. The reaction was completed and the resulting gummy material was taken into 300 ml of ether. The ethereal solution was washed three times with water and dried over CaSO4. After the solvent had been removed, the product was crystallized from toluene/hexane and an almost quantitative yield (>95%) of the desired ester was obtained as a light brown crystalline solid; m.p. 71°-74° C., NMR (CDCl3) 3.33 (S, 1H), 3.67-4.12 (m, 2H), 4.15-4.63 (m, 2H), 7.02-8.25 (m, 6H); ir (CHCl3) 1749 cm-1. No by-product was detected by NMR analysis.

Workup

  1. temperaturewas heated in an oil bath at 105°-110° C. for 10 hrs
  2. washThe ethereal solution was washed three times with water
  3. dry with materialdried over CaSO4
  4. customAfter the solvent had been removed
  5. customthe product was crystallized from toluene/hexane

Sources & evidence

ORD record
ord-4dcaabe3db6a421f9d9cb9ce800d69f8
Source dataset
uspto-grants-1984_05
Patent number
US04448982

Reaction notes

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