2-Chloroethanol → 4-(2-Hydroxyethoxy)benzenecarboxylic acid

HRID 1067147Notes

Reaction equation

HRID 1067147 reaction equation
[CH2:1](Cl)[CH2:2][OH:3].[OH:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1>[I-].[K+]>[OH:3][CH2:2][CH2:1][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 342-ChloroethanolHCID 1354-Hydroxybenzoic Acid

Product 1

HCID 43122544-(2-Hydroxyethoxy)benzenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 4875Potassium IodideCatalyst

Procedure

That is, as the reaction formula described below, ethylene chlorohydrin and 4-hydroxybenzoic acid are refluxed under heating in an aqueous alkali solution using potassium iodide as a catalyst to obtain 4-(2-hydroxyethoxy)benzoic acid, the product is then reacted with vinyl (meth)acrylate in THF (tetrahydrofuran) having added thereto lipase PS and a small amount of p-methoxyphenol to form 4-(2-propenoyloxyethoxybenzoic acid) (meth)acrylate, and by esterifying the (meth)acrylate thus obtained in methylene chloride with an isosorbide derivative in the presence of DCC (dicyclohexylcarbodiimide) and DMAP (dimethylaminopyridine), the desired product of the formula (b1) can be obtained.

Workup

  1. temperatureare refluxed
  2. temperatureunder heating in an aqueous alkali solution

Sources & evidence

ORD record
ord-a1a674910f5f4077baf2608ddf1496be
Source dataset
uspto-grants-2001_06
Patent number
US06248259B1

Reaction notes

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