Triethylamine → 5-Hydroxy-3-(4-methylthiophenoxy)benzoic acid methyl ester

HRID 2113807Notes

Reaction equation

HRID 2113807 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6](OB(O)O)=[CH:5][CH:4]=1.[CH2:13](N(CC)CC)C.[CH3:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[C:27]([OH:29])[CH:26]=C(O)[CH:24]=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:20][O:21][C:22](=[O:31])[C:23]1[CH:28]=[C:27]([OH:29])[CH:26]=[C:1]([S:2][C:3]2[CH:8]=[CH:7][C:6]([CH3:13])=[CH:5][CH:4]=2)[CH:24]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 75076Methyl 3,5-DihydroxybenzoateHCID 21939890p-Methylthiophenylboric acid

Product 1

HCID 1317270855-Hydroxy-3-(4-methylthiophenoxy)benzoic acid methyl esterYield 37.7%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

After adding 29.0 g of molecular sieves 4A, 22.0 g (0.13 mol) of p-methylthiophenylboric acid, 21.6 g (0.13 mol) of copper (II) acetate and 83.0 ml (0.59 mol) of triethylamine to a solution of 20.0 g (0.12 mol) of 3,5-dihydroxybenzoic acid methyl ester in methylene chloride (1.2 l), the mixture was stirred at room temperature overnight under an 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=2:1) to obtain 12.4 g of 5-hydroxy-3-(4-methylthiophenoxy)benzoic acid methyl ester (yield: 36%) as a yellow solid.

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=2:1)

Sources & evidence

ORD record
ord-d33e8f59d0f34d08a9791d0b6b91d1fd
Source dataset
uspto-grants-2008_10
Patent number
US07432287B2

Reaction notes

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