Hydrochloric Acid → 2-Hydroxy-5-methoxybenzaldehyde

HRID 2265798Notes

Reaction equation

HRID 2265798 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[Cl-].[Cl-].[Mg+2].C(N(CC)CC)C.[CH2:20]=[O:21].Cl>C(#N)C>[OH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[CH:20]=[O:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8471TriethylamineHCID 90154-MethoxyphenolHCID 5360315Magnesium Chloride

Product 1

HCID 956952-Hydroxy-5-methoxybenzaldehydeYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of compound p-methoxyphenol (3 g, 24.2 mmol), anhydrous magnesium dichloride (3.48 g, 37.0 mmol) and dry triethylamine (12.8 mL, 92.1 mmol) in 100 mL of acetonitrile was added dry paraformaldehyde (5 g, 167 mmol). The reaction mixture was refluxed for 8 hours and cooled down to room temperature. Then the reaction mixture was poured into 5% HCl (300 mL) and extracted with diethyl ether (200 mL) for three times. The combined organic layers were dried over anhydrous Na2SO4, filtered, and evaporated. The residue was purified by flash column chromatography (20% EtOAc in n-hexane) to yield 3.35 g of 2-hydroxy-5-methoxybenzaldehyde (91% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 8 hours
  2. extractionextracted with diethyl ether (200 mL) for three times
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash column chromatography (20% EtOAc in n-hexane)

Sources & evidence

ORD record
ord-0a53cb2e6645401a9f5910de609d760b
Source dataset
uspto-grants-2010_12
Patent number
US07858598B2

Reaction notes

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