Vanillin → HCID 18433807, compound

HRID 2172836Notes

Reaction equation

HRID 2172836 reaction equation
[O:1]=[CH:2][C:3]1[CH:11]=[CH:10][C:8]([OH:9])=[C:5]([O:6][CH3:7])[CH:4]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([CH:11]=[CH:10][C:8]=1[O:9][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:2]=[O:1]

Participants

6

Reactant 3

HCID 1183VanillinHCID 8471TriethylamineHCID 66827Phenylboronic Acid

Product 1

HCID 18433807HCID 18433807, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of vanillin (500 mg), phenylboronic acid (1.60 g) and copper(II) acetate (712 mg) in methylene chloride (10 mL) were added molecular sieve 4A (750 mg) and triethylamine (665 mg), and the mixture was stirred at room temperature for 2 days. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (50 mL). The solution was washed successively with 0.5M aqueous hydrochloric acid solution, 1M aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 3-methoxy-4-phenoxybenzaldehyde (440 mg) as a yellow solid.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washThe solution was washed successively with 0.5M aqueous hydrochloric acid solution, 1M aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-61150f8d5cbc4d34974e594d54d0fca1
Source dataset
uspto-grants-2015_06
Patent number
US09056862B2

Reaction notes

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