Ethyl Acetate → HCID 19080443, compound

HRID 404358Notes

Reaction equation

HRID 404358 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 T23.2 (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 T23.3 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-2908acfc8cb54928ad5907df6cfe5ce1
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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