4-Hydroxybenzaldehyde → 4-(Methoxymethoxy)benzaldehyde

HRID 1053709Notes

Reaction equation

HRID 1053709 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].[CH2:12](Cl)[O:13][CH3:14].O>CN(C=O)C>[CH3:12][O:13][CH2:14][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride

Product 1

HCID 2500744-(Methoxymethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-hydroxybenzaldehyde (1.22 g, 10 mmol) was dissolved in 100 ml dried DMF and stirred at room temperature. NaH (0.8 g) was added in to the reaction. After 10 min, MOMCl (1.5 ml) was added into the reaction by drop. Then the result solution was stirred at room temperature, and monitored by TLC. When the reaction was completed, 500 ml H2O was added. The resulting solution was extracted by ethyl acetate, and the organic layers were combined, dried by Na2SO4, concentrated by reduce pressure. The resulting oil was directly used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ: 3.50 (s, 3H), 5.26 (s, 2H), 7.14 (d, J=8.8 Hz, 2H), 7.83 (d, J=8.8 Hz, 2H), 9.90 (s, 1H).

Workup

  1. stirringThen the result solution was stirred at room temperature
  2. extractionThe resulting solution was extracted by ethyl acetate
  3. dry with materialdried by Na2SO4
  4. concentrationconcentrated
  5. customThe resulting oil was directly used in the next step without further purification

Sources & evidence

ORD record
ord-0c91f460bea441aa9dfe8247069fb98c
Source dataset
uspto-grants-2016_07
Patent number
US09394268B2

Reaction notes

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