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

HRID 1909570Notes

Reaction equation

HRID 1909570 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-41b83a71502547f0a08fb99ec1ae04e7
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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