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

HRID 983787Notes

Reaction equation

HRID 983787 reaction equation
[H-].[Na+].[H][H].[OH:5][C:6]1[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[O:9].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CS(C)=O>[CH2:15]([O:5][C:6]1[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[O:9])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 905792,3-DihydroxybenzaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 130703912-(Benzyloxy)-3-hydroxybenzaldehydeYield 69.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

For example, sodium hydride (0.52 g, 21.7 mmol) is added to DMSO (20 ml) followed by an aldehyde of formula 11 wherein R3, R4 and R5 are hydrogen, i.e., 2,3-dihydroxybenzaldehyde, (2.8 g, 20.2 mmol). After stirring the solution for 1 h at ambient temperature, benzyl bromide 12 (2.4 ml, 20.2 mmol) was added forming a red-brown reaction mixture which was further stirred 12 h at ambient temperature. The solution was then partitioned between ethyl acetate (200 ml) and 0.5 N hydrochloric acid (300 ml). The organic layer was separated and MgSO4, filtered and concentrated to afford a brown oil. The brown oil is purified by flash chromatography (15% ethyl acetate/hexane) to give 3.21 g of 2-benzyloxy-3-hydroxy-benzaldehyde 16.

Workup

  1. customforming a red-brown reaction mixture which
  2. stirringwas further stirred 12 h at ambient temperature
  3. customThe solution was then partitioned between ethyl acetate (200 ml) and 0.5 N hydrochloric acid (300 ml)
  4. customThe organic layer was separated
  5. filtrationMgSO4, filtered
  6. concentrationconcentrated
  7. customto afford a brown oil
  8. customThe brown oil is purified by flash chromatography (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-86f9aec7fce34861a3286563cbfa872e
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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