4-Hydroxybenzoic Acid → 2-Hydroxyethyl 4-hydroxybenzoate

HRID 1033284Notes

Reaction equation

HRID 1033284 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[CH2:11]1[O:13][CH2:12]1>C(O)(C)C>[OH:13][CH2:12][CH2:11][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 2

HCID 1354-Hydroxybenzoic AcidHCID 6354Ethylene Oxide

Product 1

HCID 2679502-Hydroxyethyl 4-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Into an autoclave, 138 parts by weight of p-hydroxybenzoic acid, 1 part by weight of Na2CO2 and 300 parts by weight of isopropanol were charged, and at 90° C., 66 parts by weight of ethylene oxide was added thereto, and the reaction was conducted. After the reaction, the mixture was cooled, and the precipitate was collected by filtration and recrystallized twice from water to obtain 55 parts by weight of p-hydroxylbenzoic acid-β-hydroxyethyl ester ##STR88## having a melting point of 141° C. The structure was confirmed by 1H-NMR.

Workup

  1. customAfter the reaction
  2. temperaturethe mixture was cooled
  3. filtrationthe precipitate was collected by filtration
  4. customrecrystallized twice from water

Sources & evidence

ORD record
ord-06662c88b742439d822a83102e60ca05
Source dataset
uspto-grants-1994_05
Patent number
US05310859

Reaction notes

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