Benzene → 3,4-Dimethoxy-5-(prop-1-yn-1-yl)benzoic acid

HRID 638936Notes

Reaction equation

HRID 638936 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].CCN(CC)CC.[CH:22]1[CH:27]=CC=C[CH:23]=1>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][O:13][C:9]1[CH:8]=[C:4]([CH:3]=[C:2]([C:23]#[C:22][CH3:27])[C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 241BenzeneHCID 8471TriethylamineHCID 2304593-Iodo-4,5-dimethoxybenzoic acid

Product 1

HCID 686858383,4-Dimethoxy-5-(prop-1-yn-1-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a stirred solution of 3-iodo-4,5-dimethoxybenzoic acid (12.32 g, 40.0 mmol) in mixture of Et3N (80 mL) and benzene (80 mL) at room temperature was added CuI (760 mg, 4 mmol) followed by Pd(PPh3)4 (924 mg, 0.8 mmol, 0.02 eq.). After stirring for 2 days under propyne atmosphere (balloon) at room temperature, the solvent was removed, the residue was suspended in 1N HCl aqueous solution (300 mL) and then extracted with EtOAc (3×100 mL). The combined organic layer wash washed with brine (300 mL), dried over Na2SO4 and then concentrated in vacuo to give 3,4-dimethoxy-5-prop-1-ynylbenzoic acid (9.7 g). The product was used without further purification.

Workup

  1. customthe solvent was removed
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic layer wash
  4. washwashed with brine (300 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40e24c14ed67436282080f6903c75424
Source dataset
uspto-grants-2010_04
Patent number
US07691843B2

Reaction notes

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