Guaiacol → HCID 22633232, compound

HRID 2417397Notes

Reaction equation

HRID 2417397 reaction equation
C([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[C:7](Br)[C:6]=1[O:14][CH3:15])(=O)C.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[OH:24].C(=O)([O-])[O-].[Cs+].[Cs+]>N1C=CC=CC=1.[Cu]=O>[OH:4][C:5]1[C:6]([O:14][CH3:15])=[CH:7][C:8]([CH:9]=[O:10])=[C:11]([O:24][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[O:17][CH3:16])[CH:12]=1

Participants

6

Reactant 3

HCID 460GuaiacolHCID 10796Cesium carbonateHCID 218837454-Acetoxy-2-bromo-3-methoxybenzaldehyde

Product 1

HCID 22633232HCID 22633232, compound

Reagents, catalysts & solvents 2

HCID 14829Copper oxideCatalystHCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of 4-acetoxy-2-bromo-3-methoxybenzaldehyde (546 mg, 2 mmol; prepared in example 105, step a), 2-methoxy-phenol (280 mg, 2 mmol) and cesium carbonate (1.3 g, 4 mmol) in 16 mL of pyridine was added copper oxide(320 mg, 4 mmol)under argon. The mixture was purged with argon for 10 min, heated at 130° C. overnight and then quenched with 5% HCl solution. The mixture was extracted with ethyl acetate, washed with 1N NaOH solution and water before drying over sodium sulfate. After the removal of the solvent, the residue was chromatographed to give the product, 4-hydroxy-5-methoxy-2-(2-methoxy-phenoxy)-benzaldehyde.

Workup

  1. customThe mixture was purged with argon for 10 min
  2. customquenched with 5% HCl solution
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with 1N NaOH solution and water
  5. dry with materialbefore drying over sodium sulfate
  6. customAfter the removal of the solvent
  7. customthe residue was chromatographed

Sources & evidence

ORD record
ord-4945bdbcafc1435cab2ad68f298c7248
Source dataset
uspto-grants-2004_11
Patent number
US06825208B2

Reaction notes

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