4-Hydroxybenzoic Acid → 2-Methoxyethyl 4-hydroxybenzoate

HRID 2164331Notes

Reaction equation

HRID 2164331 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:16][O:17][CH2:18][CH2:19]O>>[CH3:16][O:17][CH2:18][CH2:19][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

4

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 1118Sulfuric AcidHCID 80192-Methoxyethanol

Product 1

HCID 30200812-Methoxyethyl 4-hydroxybenzoate

Procedure

A mixture of 25.0 g of p-hydroxybenzoic acid, 170 g of methyl glycol (methoxyethanol) and 1 ml of sulfuric acid (conc.) was heated for 8 hours to 110°-115° C. and, after the excess methyl glycol had been distilled off under reduced pressure, was poured onto ice/water. After neutralization with sodium hydrogen carbonate, the aqueous phase was extracted by shaking several times with methylene chloride. The methylene chloride solution was treated with active carbon, concentrated by evaporation and the residue recrystallized from toluene. p-hydroxybenzoic acid 2-methyloxy-ethyl ester melting at 90°-93° C. was obtained in a yield of 27.6 g (78%).

Workup

  1. temperaturewas heated for 8 hours to 110°-115° C.
  2. distillationafter the excess methyl glycol had been distilled off under reduced pressure
  3. additionwas poured onto ice/water
  4. extractionAfter neutralization with sodium hydrogen carbonate, the aqueous phase was extracted
  5. additionThe methylene chloride solution was treated with active carbon
  6. concentrationconcentrated by evaporation
  7. customthe residue recrystallized from toluene

Sources & evidence

ORD record
ord-cc2bf14c4e0f464e90b072eca8463fc7
Source dataset
uspto-grants-1985_03
Patent number
US04503244

Reaction notes

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