Acetonitrile → HCID 15218724, compound

HRID 1741805Notes

Reaction equation

HRID 1741805 reaction equation
C(#N)C.[OH:4][CH2:5][CH2:6][O:7][C:8]1[CH:27]=[CH:26][C:11]([O:12][CH2:13][CH2:14][O:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([Cl:24])[CH:18]=2)=[CH:10][CH:9]=1.[C:28](Cl)(=[O:32])[C:29]([CH3:31])=[CH2:30]>CN1CCCC1=O>[C:28]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][O:15][C:16](=[O:25])[C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[C:19]([Cl:24])[CH:18]=2)=[CH:26][CH:27]=1)(=[O:32])[C:29]([CH3:31])=[CH2:30]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 13528Methacryloyl chlorideHCID 54127676HCID 54127676, compound

Product 1

HCID 15218724HCID 15218724, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A 300-ml eggplant type flask was charged with 16.3 g of 3-chloro-4-hydroxybenzoic acid methyl ester, 87 g of 1,4-(2-hydroxyethoxy)benzene and further with 0.8 g of PTD (p-toluenesulfonic acid monohydrate) as a catalyst to form a mixture. The mixture was stirred with heating on an oil bath, externally regulated at a temperature of 150° C., to react the mixture for 5 hours. The reaction mixture was poured into ice water followed by extracting with ethyl acetate, drying over anhydrous magnesium sulfate, concentrating and separating with a column using ethylacetate/n-hexane to obtain 29 g of 3-chloro-4-hydroxybenzoic acid 2-[4-(β-hydroxyethoxy)-phenoxy]ethyl ester (melting point: 87° to 88° C.). To 50 ml of an acetonitrile solution containing 10 g of the 3-chloro-4-hydroxybenzoic acid 2-[4-(β-hydroxyethoxy)-phenoxy]ethyl ester, 13.9 g of N-methylpyrrolidone and further 8.78 g of methacrylic acid chloride were added with stirring to form a solution. The solution was stirred at 40° C. for 8 hours to react the solution. Thereafter, excess methacrylic acid chloride was removed by means of vacuum distillation. The reaction mixture remaining therein was poured into ice water and the precipitated crystals were obtained by filtration. The crystals were recrystallized with ethylacetate/n-hexane to obtain 3-chloro-4-hydroxybenzoic acid 2-[4-(β-methacryloyloxyethoxy)phenoxy]ethyl ester (melting point: 105° to 106° C.).

Workup

  1. additionwere added
  2. customto form a solution
  3. stirringThe solution was stirred at 40° C. for 8 hours
  4. customto react the solution
  5. customThereafter, excess methacrylic acid chloride was removed by means of vacuum distillation
  6. additionThe reaction mixture remaining therein was poured into ice water
  7. customthe precipitated crystals were obtained by filtration
  8. customThe crystals were recrystallized with ethylacetate/n-hexane

Sources & evidence

ORD record
ord-d7c56ab5505a401191e786c2b21e9612
Source dataset
uspto-grants-1994_08
Patent number
US05334749

Reaction notes

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