Benzyl Bromide → 5-(Benzyloxy)-2-methoxybenzaldehyde

HRID 1165619Notes

Reaction equation

HRID 1165619 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].ClCCl.O>[CH2:12]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 3583415-Hydroxy-2-Methoxybenzaldehyde

Product 1

HCID 109666945-(Benzyloxy)-2-methoxybenzaldehyde

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 5-hydroxy-2-methoxybenzaldehyde (306.6 g, prepared by the method of Ulrich et al, J.Org.Chem., 1974, 39, 2437), benzyl bromide (355.8 g) add Adogen 464 (48.5 g) in dichloromethane (600 ml) was added a solution of sodium hydroxide (123.5 g) in water (500 ml). The mixture became warm and the suspension dissolved; additional dichloromethane (300 ml) was added to prevent crystallisation of the benzylated product. After 2 hours, the organic layer was removed, washed twice wit water, once with saturated sodium chloride solution, then dried with anhydrous magnesium sulphate. The solution was concentrated, then treated with petroleum spirit to give 5-benzyloxy-2-methoxybenzaldehyde (445.7 g, 91%, m.p. 99°-100°.

Workup

  1. customprepared by the method of Ulrich et al, J.Org.Chem
  2. temperatureThe mixture became warm
  3. dissolutionthe suspension dissolved
  4. customcrystallisation of the benzylated product
  5. customthe organic layer was removed
  6. washwashed twice wit water
  7. dry with materialonce with saturated sodium chloride solution, then dried with anhydrous magnesium sulphate
  8. concentrationThe solution was concentrated
  9. additiontreated with petroleum spirit

Sources & evidence

ORD record
ord-a732b64c4f014541bb4ea5234e848298
Source dataset
uspto-grants-1990_03
Patent number
US04910305

Reaction notes

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