Protocatechuic Acid → Ethyl 3,4-Dihydroxybenzoate

HRID 2291897Notes

Reaction equation

HRID 2291897 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[CH2:12](O)[CH3:13].OS(O)(=O)=O>O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([O:7][CH2:12][CH3:13])=[O:6]

Participants

5

Reactant 3

HCID 72Protocatechuic AcidHCID 702EthanolHCID 1118Sulfuric Acid

Product 1

HCID 77547Ethyl 3,4-DihydroxybenzoateYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture which contained 43 g (0.28 mole) of 3,4-dihydroxybenzoic acid, 300 ml of ethanol and 0.5 ml of concentrated H2SO4 was refluxed for 48 hours. Water was trapped with 3A molecular sieves. The reaction mixture was evaporated to dryness in vacuo, and partitioned between ether and 5% NaHCO3 solution. The ether layer was evaporated to give 39 g (69%) of solid; m.p. 128°-130° C. The NMR and IR spectra were consistent with the assigned structure.

Workup

  1. temperaturewas refluxed for 48 hours
  2. customThe reaction mixture was evaporated to dryness in vacuo
  3. custompartitioned between ether and 5% NaHCO3 solution
  4. customThe ether layer was evaporated

Sources & evidence

ORD record
ord-977044b84b6d4988b36fb91d3254842a
Source dataset
uspto-grants-1989_01
Patent number
US04798892

Reaction notes

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