2-Allyl-5-methoxy-benzoic acid methyl ester → 5-Methoxy-2-propyl-benzoic acid methyl ester

HRID 2261781Notes

Reaction equation

HRID 2261781 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH2:12][CH:13]=[CH2:14]>[Pd].CO>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 1

HCID 574433022-Allyl-5-methoxy-benzoic acid methyl ester

Product 1

HCID 574433035-Methoxy-2-propyl-benzoic acid methyl esterYield 81.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To an ambient temperature suspension of 10% palladium on carbon (245 mg) in MeOH (5 mL) is added a solution of 2-Allyl-5-methoxy-benzoic acid methyl ester (440 mg, 2.13 mmol) in MeOH (5 mL) in one portion. The reaction is placed under an atmosphere of hydrogen gas and is stirred overnight. The reaction mixture is filtered through Celite® and concentrated to yield the title compound (361 mg, 81%). 1H NMR (400 MHz, CDCl3) δ 7.38 (d, 1H, J=3.1 Hz), 7.15 (d, 1H, J=8.4 Hz), 6.97 (dd, 1H, J=8.6, 2.9 Hz), 3.89 (s, 3H), 3.82 (s, 3H), 2.88-2.82 (m, 2H), 1.65-1.53 (m, 2H), 0.95 (t, 3H, J=7.5 Hz).

Workup

  1. filtrationThe reaction mixture is filtered through Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f40d981d04cd4dbca28e1de9541bb8da
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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