Benzyl Bromide → 2-(Benzyloxy)-3-methoxybenzaldehyde

HRID 5894

Reaction equation

HRID 5894 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:6]([O:7][CH3:8])[C:4]=1[OH:5].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH3:8][O:7][C:6]1[C:4]([O:5][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:3]([CH:11]=[CH:10][CH:9]=1)[CH:2]=[O:1]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8991o-VanillinHCID 11430Potassium Carbonate

Product 1

HCID 12680872-(Benzyloxy)-3-methoxybenzaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 196.0 g (1.30 mole) of o-vanillin (Aldrich), 200 g of benzyl bromide (Aldrich), 500 g of anhydrous potassium carbonate and 1,500 mL of absolute ethanol is heated, with stirring, at reflux for 6 hours. After cooling, the supernatant is decanted and the remainder is filtered. The combined filtrate and supernatant is concentrated at reduced pressure to remove solvent. The remaining oil is extracted into 1 L of ether. The ether solution is washed with 500 mL of water, 600 mL of 1% potassium hydroxide solution, and 500 mL of water and then dried (potassium carbonate) and concentrated to give 263.4 g (84% yield) of product; mp 41°-43° C. Reported mp, 43° C. (Chem. Abstr. 62:16110a).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 6 hours
  3. temperatureAfter cooling
  4. customthe supernatant is decanted
  5. filtrationthe remainder is filtered
  6. concentrationThe combined filtrate and supernatant is concentrated at reduced pressure
  7. customto remove solvent
  8. extractionThe remaining oil is extracted into 1 L of ether
  9. washThe ether solution is washed with 500 mL of water, 600 mL of 1% potassium hydroxide solution, and 500 mL of water
  10. dry with materialdried (potassium carbonate)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-0b20c9191db0436d9a89e14bbc14aaef
Source dataset
uspto-grants-1993_09
Patent number
US05246943

Linked notes

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