HCID 14257052, compound → HCID 14257053, compound

HRID 622070Notes

Reaction equation

HRID 622070 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([O:9]CC2C=CC=CC=2)=[CH:4][C:3]=1[O:17][CH3:18].[H][H]>C(O)(=O)C.[Pd]>[Cl:8][C:7]1[CH:6]=[C:5]([OH:9])[CH:4]=[C:3]([O:17][CH3:18])[C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 14257052HCID 14257052, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14257053HCID 14257053, compoundYield 25.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2,3-dichloro-5-benzyloxyanisole (3.4 g, 0.02 mole) in acetic acid (60 ml) was added 5% palladium on carbon (2.0 g) and the mixture hydrogenated using a Parr apparatus at 20 p.s.i. of hydrogen for 3 hours. The catalyst was removed by filtration and the acetic acid evaporated at reduced pressure. The residue was dissolved in ether, extracted with 2N sodium hydroxide acidified, extracted into ether, washed with water, brine, dried over magnesium sulfate and the solvent removed by evaporation in vacuo to give 1.0 g of 3,4-dichlor-5-methoxyphenol which melted at 119°-120° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe acetic acid evaporated at reduced pressure
  3. dissolutionThe residue was dissolved in ether
  4. extractionextracted with 2N sodium hydroxide
  5. extractionextracted into ether
  6. washwashed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. customthe solvent removed by evaporation in vacuo

Sources & evidence

ORD record
ord-e7bfc124c0a140a0bdab4dc1b215a5cf
Source dataset
uspto-grants-1988_09
Patent number
US04769370

Reaction notes

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