Sodium Iodide → Benzaldehyde, 3,5-dimethoxy-4-(phenylmethoxy)-

HRID 1647295Notes

Reaction equation

HRID 1647295 reaction equation
[CH:1](=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Na+].[I-].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:14]([O:8][C:7]1[C:9]([O:10][CH3:11])=[CH:12][C:2]([CH:1]=[O:13])=[CH:3][C:4]=1[O:5][CH3:6])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 8655SyringaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 3014502Benzaldehyde, 3,5-dimethoxy-4-(phenylmethoxy)-Yield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of syringaldehyde (3.64 g, 20 mmol), benzyl chloride (2.52 g 20 mmol), NaI (2 g) and potassium carbonate (2.76 g, 20 mmol) in anhydrous acetone (60 mL) were refluxed for 5 h and cooled to room temperature. The solid materials were removed by filtration, the filtrate was concentrated and the residue was purified by chromatography on silica gel (230-400 mesh, 50 g) using 5% EtOAc in hexane as the eluent to obtain 13j (4.3 g, 79%); mp 62°-63° C.

Workup

  1. temperaturewere refluxed for 5 h
  2. customThe solid materials were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by chromatography on silica gel (230-400 mesh, 50 g)

Sources & evidence

ORD record
ord-1306368306da485faa2df94775c76889
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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