Benzene → 5-[2-(2,5-Dimethoxyphenyl)ethinyl]-2-hydroxybenzoic acid methyl ester

HRID 375995

Reaction equation

HRID 375995 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[C:11]#[CH:12].I[C:14]1[CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:17]([OH:24])=[CH:16][CH:15]=1.C1C=CC=CC=1.C(N(CC)CC)C>O=O.[Cu]I>[CH3:22][O:21][C:19](=[O:20])[C:18]1[CH:23]=[C:14]([C:12]#[C:11][C:4]2[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH:15]=[CH:16][C:17]=1[OH:24]

Participants

7

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 248910Methyl 5-IodosalicylateHCID 110949512,5-Dimethoxyphenylacetylene

Product 1

HCID 153840065-[2-(2,5-Dimethoxyphenyl)ethinyl]-2-hydroxybenzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 977OxygenSolvent

Procedure

Under argon atmosphere 240 mg of 2,5-dimethoxyphenylacetylene and 493 mg of methyl 5-iodosalicylate are dissolved in 20 ml of oxygen-free and dry benzene. The mixture is treated with 85 mg of tetrakis (triphenylphosphine)palladium, 20 mg of copper(I)iodide and 450 mg of triethylamine, stirred at room temperature overnight and then poured onto 100 ml of aqueous pH 7 buffer. After extraction with ethyl acetate and purification by chromatography on silicagel, 5-[2-(2,5-dimethoxyphenyl)ethinyl]-2-hydroxybenzoic acid methyl ester is obtained (colorless crystals of M.P. 105°-108°).

Workup

  1. additionpoured onto 100 ml of aqueous pH 7 buffer
  2. extractionAfter extraction
  3. customwith ethyl acetate and purification by chromatography on silicagel

Sources & evidence

ORD record
ord-00b5aedde9b640c795ea84266ba6a003
Source dataset
uspto-grants-1996_01
Patent number
US05488135

Linked notes

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