Benzene → ethyl 2-phenoxybenzoate

HRID 2081638Notes

Reaction equation

HRID 2081638 reaction equation
[O:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17]1C=CC=C[CH:18]=1.S(Cl)(Cl)=O>CN(C=O)C.C(O)C>[CH2:17]([O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=1[O:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:18]

Participants

6

Reactant 3

HCID 241BenzeneHCID 24386Thionyl ChlorideHCID 752372-Phenoxybenzoic acid

Product 1

HCID 2760340ethyl 2-phenoxybenzoateYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 2-phenoxybenzoic acid (7.71 g; 0.036 mol) dry benzene (80 ml), thionyl chloride (4.76 g; 0.04 mol) and DMF (2 drops) were added, and the resultant mixture was stirred under reflux for 2 hours. The reaction mixture was dropwise added to dry ethanol (100 ml) under ice-cooling in 30 minutes, followed by allowing to stand overnight. The reaction mixture was concentrated under reduced pressure and, after addition of a 4% aqueous sodium hydrogen carbonate solution (150 ml) thereto, extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give ethyl-2-phenoxybenzoate (8.72 g, yield, 100%) as a colorless oil.

Workup

  1. additionwere added
  2. temperatureunder reflux for 2 hours
  3. temperaturecooling in 30 minutes
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionafter addition of a 4% aqueous sodium hydrogen carbonate solution (150 ml)
  6. extractionextracted with methylene chloride
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2b739b22fcb3492cba4508f661ca920c
Source dataset
uspto-grants-1993_02
Patent number
US05185342

Reaction notes

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