Benzyl Bromide → 3-Benzyloxy-4-methoxybenzaldehyde

HRID 1684059Notes

Reaction equation

HRID 1684059 reaction equation
C1OCCOCCOCCOCCOCCOC1.[OH-].[K+].[O:21]=[CH:22][C:23]1[CH:31]=[CH:30][C:27]([O:28][CH3:29])=[C:25]([OH:26])[CH:24]=1.[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1COCC1>[CH2:32]([O:26][C:25]1[CH:24]=[C:23]([CH:31]=[CH:30][C:27]=1[O:28][CH3:29])[CH:22]=[O:21])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 12127IsovanillinHCID 14797Potassium HydroxideHCID 2855718-Crown-6

Product 1

HCID 806713-Benzyloxy-4-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

18--Crown-6 ether (0.14 g, 0.00052 mols) and potassium hydroxide (1.35 g, 0.024 mols) is added to a stirred solution of isovanillin (201) (2.0 g, 0.013 mols) in THF (20 ml) at 0° C. The reacton becomes cloudy and turns bright yellow. Benzyl bromide (1.69 ml, 0.0143 mols) is added dropwise to the reaction at 0° C. After one hour, the ice bath is removed and the reaction is stirred at room temperature overnight. The reaction is diluted with ethyl acetate and washed with water and 10% HCl followed by brine solution. The organic extract is dried over sodium sulfate, filtered, concentrated and dried in vacuo no a yellow crystalline solid (3.0471 g, 96.9%).

Workup

  1. customthe ice bath is removed
  2. additionThe reaction is diluted with ethyl acetate
  3. washwashed with water and 10% HCl
  4. extractionThe organic extract
  5. dry with materialis dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dry with materialdried in vacuo no a yellow crystalline solid (3.0471 g, 96.9%)

Sources & evidence

ORD record
ord-dc4f4d25507b46578630b41d9a3dfe3a
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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