5-Isopropenyl-2,4-dimethoxy-benzoic acid methyl ester → HCID 59263169, compound

HRID 424104Notes

Reaction equation

HRID 424104 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]([CH3:12])=[CH2:11])[C:7]([O:13][CH3:14])=[CH:6][C:5]=1[O:15][CH3:16]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[C:7]([O:13][CH3:14])=[CH:6][C:5]=1[O:15][CH3:16]

Participants

4

Reactant 1

HCID 592631485-Isopropenyl-2,4-dimethoxy-benzoic acid methyl ester

Product 1

HCID 59263169HCID 59263169, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-isopropenyl-2,4-dimethoxy-benzoic acid methyl ester (6.0 g, 25.4 mmol) in MeOH (85 ml) was shaken with 10% Pd/C under an atmosphere of H2 at room temperature for 3 hours. The catalyst was filtered through GF/A paper but a little fine powder passed through. The filtrate was passed through a small pad of silica and evaporated to dryness to yield a colourless solid. The product was purified by flash column chromatography (DCM:Petrol gradient elution) to yield 5-isopropyl-2,4-dimethoxy-benzoic acid methyl ester a colourless solid (5.5 g). 1H NMR (Me-d3-OD) 7.68 (1H, s), 6.64 (1H, s), 3.94 (3H, s), 3.91 (3H, s), 3.84 (3H, s), 3.23 (1H, sept), 1.20 (6H, d). MS: [M+H]+ 239.

Workup

  1. filtrationThe catalyst was filtered through GF/A paper
  2. customevaporated to dryness
  3. customto yield a colourless solid
  4. customThe product was purified by flash column chromatography (DCM:Petrol gradient elution)

Sources & evidence

ORD record
ord-07c9e35d349e406181e2209b8f9e48de
Source dataset
uspto-grants-2012_01
Patent number
US08101648B2

Reaction notes

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