4-Methoxyphenol → Phosphonium, tributyl[2-[(2-methyl-1-oxo-2-propen-1-yl)oxy]ethyl]-, chloride (1:1)

HRID 1422299Notes

Reaction equation

HRID 1422299 reaction equation
[Cl-].[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:32])(=[O:31])[C:28]([CH3:30])=[CH2:29]>C(#N)C>[Cl-:32].[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

5

Reactant 3

HCID 90154-MethoxyphenolHCID 13528Methacryloyl chlorideHCID 10945936HCID 10945936, compound

Product 1

HCID 22119373Phosphonium, tributyl[2-[(2-methyl-1-oxo-2-propen-1-yl)oxy]ethyl]-, chloride (1:1)

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 chloride dissolved in 500 ml of acetonitrile. The solution was heated under a normal pressure while 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 76.3 g (0.730 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.

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-9f4f9c52c9d24111ba69458d88db719f
Source dataset
uspto-grants-2000_06
Patent number
US06080885

Reaction notes

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