4-Ethynyl-3-(3-methoxypropoxy)benzoic acid → 4-Ethyl-3-(3-methoxypropoxy)benzoic acid

HRID 1158396Notes

Reaction equation

HRID 1158396 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[O:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])#[CH:2]>CCO.[OH-].[OH-].[Pd+2]>[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[O:12][CH2:13][CH2:14][CH2:15][O:16][CH3:17])[CH3:2]

Participants

4

Reactant 1

HCID 862481424-Ethynyl-3-(3-methoxypropoxy)benzoic acid

Product 1

HCID 573555384-Ethyl-3-(3-methoxypropoxy)benzoic acid

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-ethynyl-3-(3-methoxy-propoxy)-benzoic acid (1 g, 4.11 mmol) in EtOH (20 mL), Pd(OH)2 (0.1 g) is added. The resulting mixture is stirred under an hydrogen atmosphere for 15 min, then filtered and concentrated. The crude material is purified by flash chromatography on silica gel (eluent: hexane/AcOEt 2:1) to give the title compound as white powder. 1H-NMR (CDCl3, 300 MHz): δ=1.2 (t, 3H), 2.15 (p, 2H), 2.7 (q, 2H), 3.38 (s, 3H), 3.62 (t, 2H), 4.15 (t, 2H), 7.25 (d, 1H), 7.55 (s, 1H), 7.68 (d, 1H) ppm.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe crude material is purified by flash chromatography on silica gel (eluent: hexane/AcOEt 2:1)

Sources & evidence

ORD record
ord-83524dc7c7f74a54802cfc8c9837924b
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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