Phenol → HCID 4496358, compound

HRID 1777107Notes

Reaction equation

HRID 1777107 reaction equation
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13]>CN(C=O)C>[O:9]([CH:11]([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24758Sodium hydrideHCID 79040Ethyl 2-bromopropionate

Product 1

HCID 4496358HCID 4496358, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of NaH (765 mg, 31.89 mmol) in DMF (10 mL) was added phenol (1 g, 10.63 mmol) at 25° C. The mixture was heated at reflux temperature for 15 min, and then ethyl 2-bromopropanoate (2.3 g, 12.75 mmol) was added. The resulting mixture was stirred at 25° C. for another 16 h before quenching with water (50 mL). The mixture was extracted with ethyll acetate (3×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the title compound (1.8 g, 85.7%) as colorless oil which was used in next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 15 min
  3. custombefore quenching with water (50 mL)
  4. extractionThe mixture was extracted with ethyll acetate (3×20 mL)
  5. washThe combined organic layers were washed with brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ce4763a30d0e49f9b6f9c267e7265dd5
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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