3-Hydroxybenzaldehyde → 3-(Methoxymethoxy)benzaldehyde

HRID 1631200Notes

Reaction equation

HRID 1631200 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH3:16][O:17][CH2:18]Cl>CC(C)=O>[CH3:16][O:17][CH2:18][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium Carbonate

Product 1

HCID 122735133-(Methoxymethoxy)benzaldehydeYield 88.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-hydroxybenzaldehyde (5.0 g) in acetone (120 mL), potassium carbonate (8.5 g) and methoxymethyl chloride (4.0 g) were added, followed by stirring at 50° C. for 6 hours. The reaction mixture was concentrated and water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried and concentrated. The residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to thereby give the title compound (6.0 g) having the following physical properties.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue thus obtained
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-efe9fa2ea9b84df495f1bfc779f47264
Source dataset
uspto-grants-2014_07
Patent number
US08791159B2

Reaction notes

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