4-Methoxyphenol → HCID 18779287, compound

HRID 1422304Notes

Reaction equation

HRID 1422304 reaction equation
[Cl-].[CH2:2]([P+:6]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH2:9][OH:10])[CH2:3][CH2:4][CH3:5].COC1C=CC(O)=CC=1.[C:28]([Cl:33])(=[O:32])[C:29]([CH3:31])=[CH2:30]>C(#N)C>[Cl-:33].[CH2:11]([P+:6]([CH2:2][CH2:3][CH2:4][CH3:5])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:7][CH2:8][CH2:9][O:10][C:28](=[O:32])[C:29]([CH3:31])=[CH2:30])[CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 13528Methacryloyl chlorideHCID 18779298Tributyl(3-hydroxypropyl)phosphanium chloride

Product 1

HCID 18779287HCID 18779287, 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(3-hydroxypropyl)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 75.8 g (0.725 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 as above. The absence of an unreacted substance was confirmed using FT-IR, and the reaction solution was concentrated and dried with a vacuum pump to give 290.3 g of a slightly yellow liquid. The titration purity was 94.6% and the yield was 100.0%.

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
  8. concentrationthe reaction solution was concentrated
  9. customdried with a vacuum pump
  10. customto give 290.3 g of a slightly yellow liquid

Sources & evidence

ORD record
ord-d2de09b76be64c77a612f009f9b28810
Source dataset
uspto-grants-2000_06
Patent number
US06080885

Reaction notes

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