Methylhydroquinone → Ethyl (4-hydroxy-3-methylphenoxy)acetate

HRID 1876413Notes

Reaction equation

HRID 1876413 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[OH:9].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:9][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 7253MethylhydroquinoneHCID 7748Ethyl bromoacetateHCID 11430Potassium Carbonate

Product 1

HCID 59419846Ethyl (4-hydroxy-3-methylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-methylbenzene-1,4-diol (5 g, 40.2 mmol), ethyl 2-bromoacetate (1.1 eq.), and potassium carbonate (2 eq.) in acetonitrile (50 mL) was heated at 80° C. for 18 hours. The reaction was cooled to room temperature, and the acetonitrile was removed in vacuo. Water was added and the crude residue was extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to provide ethyl 2-(4-hydroxy-3-methylphenoxy)acetate (682) as a pink solid.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. customthe acetonitrile was removed in vacuo
  3. additionWater was added
  4. extractionthe crude residue was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1e0be0eca28e4cb19652333095f06874
Source dataset
uspto-grants-2012_11
Patent number
US08309600B2

Reaction notes

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