Hydrochloric Acid → 3-Hydroxy-4-(2-methoxyethoxy)benzaldehyde

HRID 1427028Notes

Reaction equation

HRID 1427028 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C(=O)([O-])[O-].[Na+].[Na+].[CH3:17][O:18][CH2:19][CH2:20]Br.Cl>CN(C)C=O.O.C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:20][CH2:19][O:18][CH3:17])[CH:5]=[O:6]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 87683,4-DihydroxybenzaldehydeHCID 10340Sodium CarbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 426255193-Hydroxy-4-(2-methoxyethoxy)benzaldehydeYield 23.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Commercially available 3,4-dihydroxybenzaldehyde (39.3 g, 285 mmol) and sodium carbonate (45.2 g, 427 mmol) were dissolved in N,N-dimethylformamide (400 mL), then commercially available 2-bromoethyl methyl ether (26.7 mL, 285 mmol) was added under nitrogen atmosphere at room temperature, and the mixture was stirred for 5 days. The mixture was cooled to 0° C. and then 2 M hydrochloric acid, ethyl acetate, and water were added for partition. The aqueous layer was extracted with ethyl acetate, then the combined organic layer was washed with a saturated saline solution and dried over anhydrous magnesium sulfate, and then filtered. The solvent was evaporated, dichloromethane was added, the precipitate was separated by filtration, and then the resultant filtrate was purified with silica gel column chromatography (n-heptane:ethyl acetate=17:3-1:1). The target fraction was concentrated under vacuum to obtain the title compound (12.9 g, 23%).

Workup

  1. customfor partition
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layer was washed with a saturated saline solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated
  7. additiondichloromethane was added
  8. customthe precipitate was separated by filtration
  9. customthe resultant filtrate was purified with silica gel column chromatography (n-heptane:ethyl acetate=17:3-1:1)
  10. concentrationThe target fraction was concentrated under vacuum

Sources & evidence

ORD record
ord-4d62c6dd4e504efebe1ea63498437478
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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