Hydrochloric Acid → 2-Hydroxy-4-methoxy-3-methylbenzaldehyde

HRID 854867Notes

Reaction equation

HRID 854867 reaction equation
C[O:2][C:3]1[C:10]([CH3:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].[Cl-].[Be+2].[Cl-].Cl>C1(C)C=CC=CC=1>[OH:2][C:3]1[C:10]([CH3:11])=[C:9]([O:12][CH3:13])[CH:8]=[CH:7][C:4]=1[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24588Beryllium ChlorideHCID 2516932,4-Dimethoxy-3-methylbenzaldehyde

Product 1

HCID 105112462-Hydroxy-4-methoxy-3-methylbenzaldehydeYield 99%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,4-dimethoxy 3-methyl benzaldehyde (3.75 g, 20.8 mmole) and beryllium chloride (5.0 g, 62.5 mmole) in anhydrous toluene (50 mL) was heated to reflux for 3.5 hour. The solvent was evaporated under reduced pressure to yield an orange residue, which was treated with 2 N HCl. The compound was extracted with methylene chloride and the organic layer was dried over anhydrous MgSO4. The filtrate was evaporated and dried in vacuo to give an orange solid (3.4 g, 99%): LCMS m/z 168.05 (M+H). 1H NMR (CDCl3/300 MHz) 11.45 (s, 1H), 9.72 (s, 1H), 7.37 (d, 1H, J=8.7 Hz), 6.57 (d, 1H, J=8.7 Hz), 3.92 (s, 3H), 2.10 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3.5 hour
  3. customThe solvent was evaporated under reduced pressure
  4. customto yield an orange residue, which
  5. extractionThe compound was extracted with methylene chloride
  6. dry with materialthe organic layer was dried over anhydrous MgSO4
  7. customThe filtrate was evaporated
  8. customdried in vacuo

Sources & evidence

ORD record
ord-6dd9123059864af29f6a404503578d21
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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