HCID 15135018, compound → HCID 57198222, compound

HRID 906094Notes

Reaction equation

HRID 906094 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:13][CH:14]=[CH2:15])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8]C)=[O:7]>CO.[Pd]>[CH3:1][O:2][C:3]1[C:4]([CH2:13][CH2:14][CH3:15])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

HCID 15135018HCID 15135018, compound

Product 1

HCID 57198222HCID 57198222, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 3-(methyloxy)-2-prop-2-en-1-ylbenzoate (100 mg, 0.48 mmol) in methanol (2 mL) was hydrogenated over 5% palladium on carbon for 15 h under atmospheric pressure. The reaction mixture was filtered and 35% aqueous potassium hydroxide (1 mL) was added. The mixture was refluxed for 1 h and then concentrated. The pH was adjusted to 2 with 6N HCl. The precipitate was filtered, washed with water and dried to give 3-(methyloxy)-2-propylbenzoic acid (35 mg, 38% yield). MS (EI) for C11H14O3: 193 (M−H)

Workup

  1. filtrationThe reaction mixture was filtered
  2. addition35% aqueous potassium hydroxide (1 mL) was added
  3. temperatureThe mixture was refluxed for 1 h
  4. concentrationconcentrated
  5. filtrationThe precipitate was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-bba5ccb260624cf79470df6012b2e040
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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