Salicylaldehyde → 2-(2-methoxyethoxy)benzaldehyde

HRID 1597874Notes

Reaction equation

HRID 1597874 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].Cl[CH2:13][CH2:14][O:15][CH3:16]>CN(C=O)C>[CH3:16][O:15][CH2:14][CH2:13][O:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 6998SalicylaldehydeHCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydride

Product 1

HCID 112638502-(2-methoxyethoxy)benzaldehydeYield 16.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-hydroxybenzaldehyde (6.11 g, 0.05 mol) in DMF (50 ml) under argon in an ice bath was added NaH (2.0 g, 0.05 mol, 60% dispersion in mineral oil), followed 1 hour later by 2-chloroethylmethyl ether (4.73 g, 0.05 mol). The reaction mixture was allowed to stand for about 2 days, then was heated at 70° C. for 7 hours. The reaction mixture was stripped to dryness, the residue was partitioned between water and CHCl3, the layers were separated and the aqueous layer was extracted with CHCl3 (2×75 ml). The product appeared to be in both layers, thus they were concentrated in vacuo and the residue was purified by column chromatography on silica gel eluting with ether to afford 1.5 g of 2-[2-(methoxy)ethoxy]benzaldehyde.

Workup

  1. customthe residue was partitioned between water and CHCl3
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted with CHCl3 (2×75 ml)
  4. concentrationwere concentrated in vacuo
  5. customthe residue was purified by column chromatography on silica gel eluting with ether

Sources & evidence

ORD record
ord-972883397d53416885c77496f072aad7
Source dataset
uspto-grants-1998_04
Patent number
US05736548

Reaction notes

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