4-Hydroxybenzaldehyde → 4-(Methoxymethoxy)benzaldehyde

HRID 1186338Notes

Reaction equation

HRID 1186338 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:19][O:20][CH2:21]Cl.O>ClCCl.C(Cl)(Cl)Cl>[CH3:19][O:20][CH2:21][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 81531Diisopropylethylamine

Product 1

HCID 2500744-(Methoxymethoxy)benzaldehydeYield 97%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

4-Hydroxybenzaldehyde (500 mg, 4.09 mmol) and diisopropylethylamine (2.85 mL, 16.4 mmol) were dissolved in dichloromethane (10 mL). To this, chloromethyl methyl ether (614 μL, 8.09 mmol) was added under a nitrogen atmosphere at 0° C. and the mixture was stirred at room temperature for 8 hours. Then, water was added to the reaction mixture, and extraction with chloroform was performed, followed by drying over anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to give 4-methoxymethoxybenzaldehyde (658 mg, yield: 97%).

Workup

  1. dry with materialby drying over anhydrous sodium sulfate
  2. customThe solvent was evaporated off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)

Sources & evidence

ORD record
ord-0227a7ab915d4280ab21219af3ffc46d
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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