Benzyl Bromide → 3,4-Bis(benzyloxy)benzoic acid

HRID 2291898Notes

Reaction equation

HRID 2291898 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1O)[C:5]([O:7][CH2:8][CH3:9])=O.[C:14]([O-:17])([O-])=[O:15].[K+].[K+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-:28].[K+]>C(C(C)=O)C.CO.O>[CH2:5]([O:7][C:8]1[CH:3]=[C:2]([CH:12]=[CH:11][C:9]=1[O:28][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:14]([OH:17])=[O:15])[C:4]1[CH:10]=[CH:11][CH:12]=[CH:2][CH:3]=1

Participants

8

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 77547Ethyl 3,4-Dihydroxybenzoate

Product 1

HCID 108541553,4-Bis(benzyloxy)benzoic acidYield 183.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

To 60 g (0.33 mole) of ethyl 3,4-dihydroxybenzoate in 50 ml of methyl ethyl ketone was added 105.5 g (0.76 mole) of K2CO3 and 168.8 g (0.76 mole) of benzyl bromide. The mixture was refluxed for 16 hours and filtered. Evaporation of the filtration gave an oil. This oil was mixed with 40 g of KOH, 350 ml of water and 350 ml of methanol and refluxed for 2.5 hours. The methanol was evaporated and the reaction mixture was acidified with concentrated HCl. The precipitate was filtered to give 101 g (92%) of the desired product; m.p. 184°-185° C. The NMR and IR spectra were consistent with the assigned structure.

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. filtrationfiltered
  3. customEvaporation of the filtration
  4. customgave an oil
  5. temperaturerefluxed for 2.5 hours
  6. customThe methanol was evaporated
  7. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-518c21e9ed0141959fef73092499a2b3
Source dataset
uspto-grants-1989_01
Patent number
US04798892

Reaction notes

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