3,4-Dihydroxybenzaldehyde → 3-Hydroxy-4-(2-methoxyethoxy)benzaldehyde

HRID 2236569Notes

Reaction equation

HRID 2236569 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[CH3:11][O:12][CH2:13][CH2:14]Br.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:14][CH2:13][O:12][CH3:11])[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 87683,4-DihydroxybenzaldehydeHCID 10340Sodium CarbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 426255193-Hydroxy-4-(2-methoxyethoxy)benzaldehydeYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An amount of 3,4-dihydroxybenzaldehyde (5.0 g, 36.2 mmol) in 20 mL of N,N′-dimethylformamide is added 2-bromoethyl methyl ether (3.4 mL, 36.2 mmol), and sodium carbonate (5.0 g, 72.4 mmol). The reaction mixture is stirred at room temperature for 3 days. After removal solids by filtration, the solution is subsequently evaporated under high-pressure vacuum to dark brown liquid. The residue is added water and acidified with 12 N HCl solution to pH˜2, then extracted 4×100 mL of EtOAc. The combined organic layer is washed with brine, dried over Mg2SO4, stirred in darko, filtered and evaporated to give yellow liquid. Purification is performed by column chromatography over silica gel using 40% EtOAc/Hex as eluent to give 2.13 g of colorless solid: mp 74-75° C.; MS (ESI) m/z 195.1 (M+H)−1

Workup

  1. customAfter removal solids
  2. filtrationby filtration
  3. customthe solution is subsequently evaporated under high-pressure vacuum to dark brown liquid
  4. additionThe residue is added water
  5. extractionextracted 4×100 mL of EtOAc
  6. washThe combined organic layer is washed with brine
  7. dry with materialdried over Mg2SO4
  8. stirringstirred in darko
  9. filtrationfiltered
  10. customevaporated
  11. customto give yellow liquid
  12. customPurification

Sources & evidence

ORD record
ord-1dc04bc8738441ccba5d05bf4c008aa3
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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