Diethylene Glycol → HCID 1714236, compound

HRID 1741802Notes

Reaction equation

HRID 1741802 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([Cl:11])[CH:5]=1.[CH2:13]([OH:19])[CH2:14][O:15][CH2:16]CO>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[OH:19][CH2:13][CH2:14][O:15][CH2:16][CH2:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([Cl:11])[CH:5]=1

Participants

4

Reactant 2

HCID 8117Diethylene GlycolHCID 77580Methyl 3-chloro-4-hydroxybenzoate

Product 1

HCID 1714236HCID 1714236, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

A 500-ml eggplant type flask was charged with 50 g of 3-chloro-4-hydroxybenzoic acid methyl ester, 285 g of diethyleneglycol and further with 2.5 g of PTS (p-toluenesulfonic acid monohydrate) as a catalyst to form a mixture. The mixture was heated with stirring on an oil bath, externally regulated at a temperature of 150° C., to react the mixture for 5 hours. Thereafter, excess diethylene glycol therein was removed by means of vacuum distillation. The residue therein was poured into ice water and the precipitated crystals were recrystallized using benzene/ethanol to obtain 49 g of 3-chloro-4-hydroxybenzoic acid [2-(2-hydroxyethoxy)ethyl]-ester (melting point: 77.5° to 78° C.). To 100 ml of an acetonitrile solution containing 30 g of the 3-chloro-4-hydroxybenzoic acid [2-(2-hydroxyethoxy)ethyl]ester, 57.2 g of N-methylpyrrolidone and further 36 g of methacrylic acid chloride were added with stirring to form a solution. The solution was stirred for 8 hours at 40° C. 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 ethyl acetate/n-hexane to obtain 3-chloro-4-hydroxybenzoic acid [2-(2-methacryloyloxyethoxy)ethyl]ester (melting point: 57° to 58.5° C.).

Workup

  1. customto form a mixture
  2. temperatureThe mixture was heated
  3. customexternally regulated at a temperature of 150° C.
  4. customto react the mixture for 5 hours
  5. customThereafter, excess diethylene glycol therein was removed by means of vacuum distillation
  6. additionThe residue therein was poured into ice water
  7. customthe precipitated crystals were recrystallized

Sources & evidence

ORD record
ord-174f9239eb634f85a87e843f8fd94bb2
Source dataset
uspto-grants-1994_08
Patent number
US05334749

Reaction notes

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