Hydroquinone → Propanoic acid, 2-(4-hydroxyphenoxy)-, ethyl ester

HRID 1534309Notes

Reaction equation

HRID 1534309 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].[CH3:9][CH2:10][O:11][C:12]([CH:14](Br)[CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[OH:2][C:1]1[CH:8]=[CH:7][C:5]([O:6][CH:14]([CH3:15])[C:12]([O:11][CH2:10][CH3:9])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 3017597Propanoic acid, 2-(4-hydroxyphenoxy)-, ethyl esterYield 25.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of hydroquinone (12.2 g), ethyl DL-2-bromopropionate (10 g) and potassium carbonate (50 g) in methylethylketone (100 ml) was stirred under reflux for 5 hours. After removal of insoluble materials by filtration, the filtrate was concentrated by distillation. The residue was dissolved in ethyl acetate, washed with 5% aqueous hydrochloric acid and concentrated to remove ethyl acetate. The residue was purified by silica gel chromatography (eluent: 20% ethyl acetate : 80% n-hexane) to give ethyl 2-(4-hydroxyphenoxy)propionate (3.0 g). Yield, 26%.

Workup

  1. temperatureunder reflux for 5 hours
  2. customAfter removal of insoluble materials
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated by distillation
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with 5% aqueous hydrochloric acid
  7. concentrationconcentrated
  8. customto remove ethyl acetate
  9. customThe residue was purified by silica gel chromatography (eluent: 20% ethyl acetate : 80% n-hexane)

Sources & evidence

ORD record
ord-bdb2625d188647a795aa39423bf01914
Source dataset
uspto-grants-1992_02
Patent number
US05089043

Reaction notes

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