Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-methylacrylate → HCID 58566718, compound

HRID 1909525Notes

Reaction equation

HRID 1909525 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[H][H]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([CH3:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 2

HCID 67406957Ethyl 3-(3-chloro-4-hydroxyphenyl)-2-methylacrylateHCID 178418361HCID 178418361, compound

Product 1

HCID 58566718HCID 58566718, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the alkene (515) (0.481 g, 2.0 mmol) in ethyl acetate (20 mL) was added Pd/C (48 mg, 10% Degussa type). A balloon of hydrogen gas was added and the reaction was evacuated and back-filled with hydrogen three times. The reaction was stirred overnight under a hydrogen balloon at room temperature, then filtered through a pad of celite and concentrated in vacuo to provide the intermediate ethyl 3-(3-chloro-4-hydroxyphenyl)-2-methylpropanoate (516A) (0.470 g, 96.9%) as a white solid. LC-MS ESI m/z: found 243.2 [M+H]+.

Workup

  1. customthe reaction was evacuated
  2. additionback-filled with hydrogen three times
  3. filtrationfiltered through a pad of celite
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31f96067d1a249dc85644b351df2352e
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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