4-Methoxyphenol → HCID 22119379, compound

HRID 1422300Notes

Reaction equation

HRID 1422300 reaction equation
[Cl-].[CH2:2]([P+:10]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:11][CH2:12][OH:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].COC1C=CC(O)=CC=1.[C:39]([Cl:44])(=[O:43])[C:40]([CH3:42])=[CH2:41]>C(#N)C>[Cl-:44].[CH2:22]([P+:10]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:11][CH2:12][O:13][C:39](=[O:43])[C:40]([CH3:42])=[CH2:41])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 13528Methacryloyl chlorideHCID 18779281HCID 18779281, compound

Product 1

HCID 22119379HCID 22119379, 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-octyl(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 42.3 g (0.405 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 by FT-IR, and the reaction solution was concentrated and dried with a vacuum pump to give 209.2 g of a slightly yellow viscous liquid. The titration purity was 97.1% and the yield was 96.6%.

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 209.2 g of a slightly yellow viscous liquid

Sources & evidence

ORD record
ord-c8a297eabbcc4062abbaeee6b5e830ce
Source dataset
uspto-grants-2000_06
Patent number
US06080885

Reaction notes

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