2,5-Dimethoxybenzaldehyde → 5-Hydroxy-2-Methoxybenzaldehyde

HRID 1178461Notes

Reaction equation

HRID 1178461 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11]C)=[CH:7][C:4]=1[CH:5]=[O:6]>S(=O)(=O)(O)O>[OH:11][C:8]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[C:4]([CH:7]=1)[CH:5]=[O:6]

Participants

3

Reactant 1

HCID 667262,5-Dimethoxybenzaldehyde

Product 1

HCID 3583415-Hydroxy-2-MethoxybenzaldehydeYield 32%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

Concentrated sulfuric acid (110 ml) was added to 2,5-dimethoxybenzaldehyde (20.17 g, 0.121 mol) with cooling in an ice water bath. The resulting red suspension was stirred at 50° C. for 46 h. The reaction contents were poured over ice and extracted with diethyl ether. The ether layer was extracted with 1N sodium hydroxide (200 ml). The basic extract was acidified by addition of 3N hydrochloric acid and extracted with diethyl ether (2×). The ether extracts were combined and dried over MgSO4. After filtration, the solvent was removed in vacuo to give 5-hydroxy-2-methoxybenzaldehyde (5.85 g, 32%) as an orange solid.

Workup

  1. temperaturewith cooling in an ice water bath
  2. customThe reaction contents
  3. additionwere poured over ice
  4. extractionextracted with diethyl ether
  5. extractionThe ether layer was extracted with 1N sodium hydroxide (200 ml)
  6. extractionThe basic extract
  7. additionwas acidified by addition of 3N hydrochloric acid
  8. extractionextracted with diethyl ether (2×)
  9. dry with materialdried over MgSO4
  10. filtrationAfter filtration
  11. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b65e4b2d5b734cd1ac7f6fbeebf8b41b
Source dataset
uspto-grants-2007_10
Patent number
US07276528B2

Reaction notes

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