Iodine → HCID 22119382, compound

HRID 1422303Notes

Reaction equation

HRID 1422303 reaction equation
[I-:1].[CH2:2]([P+:6]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:7][CH2:8][OH:9])[CH2:3][CH2:4][CH3:5].COC1C=CC(O)=CC=1.[C:27](Cl)(=[O:31])[C:28]([CH3:30])=[CH2:29].II>C(#N)C>[I-:1].[CH2:10]([P+:6]([CH2:2][CH2:3][CH2:4][CH3:5])([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:7][CH2:8][O:9][C:27](=[O:31])[C:28]([CH3:30])=[CH2:29])[CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 807IodineHCID 90154-MethoxyphenolHCID 13528Methacryloyl chlorideHCID 18779289HCID 18779289, compound

Product 1

HCID 22119382HCID 22119382, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Into a 1 L-four-necked flask equipped with a stirrer, a thermometer and a distillation line, was added the obtained tri-n-butyl(2-hydroxyethyl)phosphonium iodide dissolved in 500 ml of acetonitrile. The solution was heated under a normal pressure with stirring and about 200 ml of acetonitrile was distilled. A condenser having a calcium chloride tube was installed, 1.5 g of hydroquinone monomethyl ether was added as a polymerization inhibitor, and 76.4 g (0.731 mol) of methacryloyl chloride was added thereto dropwise at 50° C. over 2 hours through a dropping funnel, then the solution was maturated for 3 hours at the same temperature. Upon dropping, yellow coloration that was believed to have been caused by isolation of iodine occurred.

Workup

  1. customInto a 1 L-four-necked flask equipped with a stirrer
  2. temperatureThe solution was heated under a normal pressure
  3. distillationabout 200 ml of acetonitrile was distilled
  4. customA condenser having
  5. customa calcium chloride tube was installed
  6. additionwas added
  7. waitthe solution was maturated for 3 hours at the same temperature

Sources & evidence

ORD record
ord-e9dcd4d8abe5410a93ec44f2db58a855
Source dataset
uspto-grants-2000_06
Patent number
US06080885

Reaction notes

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