Benzyl Bromide → Benzyl 2-formylbenzoate

HRID 231404

Reaction equation

HRID 231404 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([OH:3])=[O:2].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=[O:7])([O:3][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:2]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8406Phthalaldehydic acidHCID 11430Potassium Carbonate

Product 1

HCID 246096Benzyl 2-formylbenzoateYield 84.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-carboxybenzaldehyde (15.00 g, 0.100 moles), benzyl bromide (20.52 g, 0.120 moles) and potassium carbonate (41.46 g, 0.300 moles) in 250 ml of acetone under nitrogen in a 500 ml round-bottom flask equipped with a magnetic stirrer was refluxed for 6 hours and then stirred at room temperature overnight. The mixture was then filtered through Celite and the filtrate concentrated in vacuo to remove the acetone. The remaining yellow oil was dissolved in ether (200 ml) and this solution washed with saturated sodium bicarbonate solution (1×50 ml), saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo to give 20.4 g of the product as a yellow oil.

Workup

  1. customequipped with a magnetic stirrer
  2. temperaturewas refluxed for 6 hours
  3. filtrationThe mixture was then filtered through Celite
  4. concentrationthe filtrate concentrated in vacuo
  5. customto remove the acetone
  6. dissolutionThe remaining yellow oil was dissolved in ether (200 ml)
  7. washthis solution washed with saturated sodium bicarbonate solution (1×50 ml), saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a445ef4974ce4d15b7c1f5befa2f0893
Source dataset
uspto-grants-1989_07
Patent number
US04846873

Linked notes

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