Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-(4-Hydroxy-3,5-diiodo-phenyl)-acrylic acid methyl ester

HRID 1839915

Reaction equation

HRID 1839915 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([I:11])[C:9]=1[OH:10])[CH:5]=O.[CH3:12][O:13][C:14]([CH:16]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:15]>C1C=CC=CC=1>[CH3:12][O:13][C:14](=[O:15])[CH:16]=[CH:5][C:4]1[CH:3]=[C:2]([I:1])[C:9]([OH:10])=[C:8]([I:11])[CH:7]=1

Participants

4

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 747604-Hydroxy-3,5-diiodobenzaldehyde

Product 1

HCID 698811613-(4-Hydroxy-3,5-diiodo-phenyl)-acrylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 50 mL round bottomed flask equipped with a Teflon coated magnetic stirring bar, a reflux condenser and a rubber septum was charged with 3,5-diiodo-4-hydroxybenzaldehyde (1 g, 2.68 mmol), methyl (triphenylphosphoranylidene) acetate (1.79 g, 5.36 mmol) and benzene (30 mL). The reaction mixture was heated to a gentle reflux for 24 h. The reaction mixture was cooled to ambient temperature and concentrated to dryness. The title compound obtained was a white solid (891 mg, 78%) after the crude material was subjected to flash chromatography (SiO2, using 20% EtOAc/Hex as the eluent).

Workup

  1. customA 50 mL round bottomed flask equipped with a Teflon coated magnetic stirring bar, a reflux condenser
  2. temperatureThe reaction mixture was heated to
  3. temperaturea gentle reflux for 24 h
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-85410c82bdca4c9f91a50dfb5b13f0bb
Source dataset
uspto-grants-2004_01
Patent number
US06677473B1

Linked notes

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