Ethyl Acetate → HCID 19080443, compound

HRID 1662404Notes

Reaction equation

HRID 1662404 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH:12]=[C:13]([CH3:15])[CH3:14].CCOC(C)=O>[Pd]>[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][CH:13]([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 57467626Methyl 4-hydroxy-3-(2-methylprop-1-en-1-yl)benzoate

Product 1

HCID 19080443HCID 19080443, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a stirred solution of methyl 4-hydroxy-3-(2-methylprop-1-enyl)benzoate 66.20B (0.320 g, 1.6 mmol) in EtOAc (2.00 mL, 20 mmol) at 23° C. was added palladium on carbon (0.017 g, 0.16 mmol). The reaction was stirred under an atmosphere of hydrogen (0.0031 g, 1.6 mmol) for 16 hours. The reaction mixture was then filtered and concentrated in vacuo to give a clear oil. The residue was purified on silica gel (0-20% EtOAc in hexanes) to yield 66.20C as a colorless oil (0.256 g, 79% yield)

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated in vacuo
  3. customto give a clear oil
  4. customThe residue was purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-753b42a4b0a0428ebfb14b822e109a5f
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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