3-Hydroxybenzaldehyde → 3-(Methoxymethoxy)benzaldehyde

HRID 2252535Notes

Reaction equation

HRID 2252535 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[H-].[Na+].[CH3:12][O:13][CH2:14]Cl.O>O1CCCC1>[CH3:12][O:13][CH2:14][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride

Product 1

HCID 122735133-(Methoxymethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-hydroxybenzaldehyde (1.0 g) in tetrahydrofuran (25 mL) was added sodium hydride (374 mg) at 0° C. and the mixture was stirred at 0° C. for 20 minutes. Methoxymethylchloride (0.92 mL) was added to the reaction mixture, which was stirred for 30 minutes at room temperature. The reaction mixture was poured into cold water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=8:1→5:1) to give the title compound (1.36 g) having the following physical data.

Workup

  1. stirringwas stirred for 30 minutes at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=8:1→5:1)

Sources & evidence

ORD record
ord-29fc555b140b45e5bc68043e87218530
Source dataset
uspto-grants-2008_01
Patent number
US07323456B2

Reaction notes

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