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

HRID 1995103Notes

Reaction equation

HRID 1995103 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°-5° 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-82a26606bc5d44b9857bb965307a30fd
Source dataset
uspto-grants-1983_09
Patent number
US04402974

Reaction notes

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