Sodium hydride → 4-(Benzyloxy)-3-(3-methoxypropoxy)benzaldehyde

HRID 725608Notes

Reaction equation

HRID 725608 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[OH:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:20][O:21][CH2:22][CH2:23][CH2:24]Br>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][C:10]=1[O:17][CH2:24][CH2:23][CH2:22][O:21][CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5245511-Bromo-3-methoxypropaneHCID 5613694-Benzyloxy-3-hydroxybenzaldehyde

Product 1

HCID 214586084-(Benzyloxy)-3-(3-methoxypropoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 28.8 g of 4-benzyloxy-3-hydroxy-benzaldehyde in 100 ml of dimethylformamide is added dropwise to a suspension of 5.54 g of NaH (60% dispersion in mineral oil) in 150 ml of absolute dimethylformamide. The reaction mixture is stirred at room temperature. After 30 minutes, a solution of 29 g of 3-methoxybromopropane in 120 ml of dimethylformamide is added thereto, and the mixture is stirred at room temperature for a further 4 hours and is then concentrated by evaporation under reduced pressure. The residue is partitioned between diethyl ether and water. The combined organic phases are dried over sodium sulfate and concentrated by evaporation, and the residue is purified by FC (100 g of silica gel, dichloromethane), yielding the title compound, which crystallises spontaneously: Rf (dichloromethane/diethyl ether)=0.44.

Workup

  1. stirringthe mixture is stirred at room temperature for a further 4 hours
  2. concentrationis then concentrated by evaporation under reduced pressure
  3. customThe residue is partitioned between diethyl ether and water
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated by evaporation
  6. customthe residue is purified by FC (100 g of silica gel, dichloromethane)

Sources & evidence

ORD record
ord-faf4937201404705974201b8e408253e
Source dataset
uspto-grants-1998_01
Patent number
US05705658

Reaction notes

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