Protocatechuic Acid → Ethyl 3,4-Dihydroxybenzoate

HRID 615941Notes

Reaction equation

HRID 615941 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 3 Å 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-aef9fb3600fc4d0a84ad218442d5ce08
Source dataset
uspto-grants-1985_02
Patent number
US04501912

Reaction notes

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