Protocatechuic Acid → 3,4-Bis(benzyloxy)benzoic acid

HRID 1056471Notes

Reaction equation

HRID 1056471 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](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:12]([O:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH2:5][C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=1)[C:5]([OH:7])=[O:6])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 72Protocatechuic AcidHCID 7498Benzyl BromideHCID 11430Potassium Carbonate

Product 1

HCID 108541553,4-Bis(benzyloxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,4-Dihydroxy benzoic acid, benzyl bromide, and potassium carbonate were dissolved in acetonitrile, and the solution was refluxed for 18 hours. The reaction solution was then cooled to room temperature and filtered. The solution was then concentrated and diluted with hexanes, resulting in a solid that was collected by filtration. The solid was then recrystallized in the mixture of THF and hexanes, giving rise to a pure product.

Workup

  1. temperaturethe solution was refluxed for 18 hours
  2. filtrationfiltered
  3. concentrationThe solution was then concentrated
  4. additiondiluted with hexanes
  5. customresulting in a solid
  6. filtrationthat was collected by filtration
  7. customThe solid was then recrystallized in the mixture of THF and hexanes
  8. customgiving rise to a pure product

Sources & evidence

ORD record
ord-7d1dcf96a0664c3dadfa78a829763baf
Source dataset
uspto-grants-2016_07
Patent number
US09399044B2

Reaction notes

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