Hydrochloric Acid → 2-Hydroxy-5-methoxybenzaldehyde

HRID 869377Notes

Reaction equation

HRID 869377 reaction equation
[Mg+2].[Cl-].[Cl-].[CH2:4]=[O:5].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Cl>CC#N>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][C:10]=1[CH:4]=[O:5]

Participants

6

Reactant 4

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

Product 1

HCID 956952-Hydroxy-5-methoxybenzaldehydeYield 62.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of MgCl2 (3.48 g, 37.0 mmol), TEA (12.8 mL, 92.1 mmol) and paraformaldehyde (5 g, 167 mmol) in MeCN (100 mL) was added 4-methoxy-phenol (3 g, 24.2 mmol). The mixture was refluxed for 8 hours, cooled to room temperature, then poured into 5% HCl (300 mL), extracted with ethyl acetate (200 mL×3). The combined organic layer was dried, concentrated and purified by column chromatography on silica gel (ethyl acetate/n-hexane=1/5) to give 2.3 g of 2-hydroxy-5-methoxy-benzaldehyde (4A).

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. extractionextracted with ethyl acetate (200 mL×3)
  3. customThe combined organic layer was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography on silica gel (ethyl acetate/n-hexane=1/5)

Sources & evidence

ORD record
ord-566130b1ba954977a46e1444734cf386
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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