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

HRID 346324Notes

Reaction equation

HRID 346324 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-methoxybenzaldehydeYield 91%

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) and 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 with 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
  2. temperatureThe mixture became warm
  3. dissolutionthe suspension dissolved
  4. customcrystallisation of the benzylated product
  5. customthe organic layer was removed
  6. washwashed twice with water, once with saturated sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulphate The solution
  8. concentrationwas concentrated
  9. additiontreated with petroleum spirit

Sources & evidence

ORD record
ord-acb2eb4a36574384ae2cede7d79fd45d
Source dataset
uspto-grants-1991_10
Patent number
US05061798

Reaction notes

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