Triethylamine → HCID 87544705, compound

HRID 2354998Notes

Reaction equation

HRID 2354998 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9]B(O)O)=[CH:5][CH:4]=1)=[O:2].C(N(CC)CC)C.[CH3:20][O:21][C:22](=[O:34])[C:23]1[CH:28]=[C:27](O)[CH:26]=[C:25]([O:30][CH:31]([CH3:33])[CH3:32])[CH:24]=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:20][O:21][C:22](=[O:34])[C:23]1[CH:24]=[C:25]([O:30][CH:31]([CH3:32])[CH3:33])[CH:26]=[C:27]([O:9][C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)[CH:28]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21940015p-Formylphenylboric acidHCID 23072925Methyl 3-hydroxy-5-isopropoxybenzoate

Product 1

HCID 87544705HCID 87544705, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

After adding 1.05 g of molecular sieves 4A, 1.00 g (6.70 mol) of p-formylphenylboric acid, 605 mg (3.30 mol) of copper (II) acetate and 2.32 ml (16.6 mol) of triethylamine to a solution of 700 mg (3.30 mmol) of the obtained phenol compound in methylene chloride (30 ml), the mixture was stirred at room temperature overnight under a oxygen atmosphere. The reaction mixture was filtered and then concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=5:1) to obtain 593 mg of 3-(4-formylphenoxy)-5-isopropoxybenzoic acid methyl ester (yield: 57%) as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=5:1)

Sources & evidence

ORD record
ord-31f5d020815848ba9699340f1cf3ec14
Source dataset
uspto-grants-2010_07
Patent number
US07754743B2

Reaction notes

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