Ethyl Acetate → Ethyl 2-ethoxy-4-phenylbenzoate

HRID 1816670Notes

Reaction equation

HRID 1816670 reaction equation
Cl[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([O:13][CH2:14][CH3:15])[CH:3]=1.[C:16]1(OB(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(OCC)(=O)C>O1CCOCC1.O>[CH2:14]([O:13][C:4]1[CH:3]=[C:2]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:15]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 78412Phenyl dihydrogen orthoborateHCID 22494013HCID 22494013, compound

Product 1

HCID 22494159Ethyl 2-ethoxy-4-phenylbenzoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

0.50 g of ethyl 4-chloro-2-ethoxybenzoate, 0.31 g of phenylboric acid, 85 mg of 1,1-bis(diphenylphosphino)ferrocene dichloronickel and 1.4 g of potassium phosphate were dissolved in 8 ml dioxane, followed by stirring at 95° C. for 1 hour in a nitrogen atmosphere. After cooling the reaction solution to room temperature, ethyl acetate and water were added thereto. The mixture was filtered through Celite, and the mother liquor was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (9:1), ethyl 2-ethoxy-4-phenylbenzoate was obtained. Then, the resulting ethyl 2-ethoxy-4-phenylbenzoate was dissolved in 4 ml ethanol, and 2 ml of 1N sodium hydroxide was added thereto, followed by stirring at room temperature for 6 hours. The reaction mixture was ice-cooled and neutralized with 1N hydrochloric acid, followed by extracting with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and the solvent was evaporated, to give 0.22 g of 2-ethoxy-4-phenylbenzoic acid.

Workup

  1. temperatureAfter cooling the reaction solution to room temperature
  2. filtrationThe mixture was filtered through Celite
  3. extractionthe mother liquor was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. washfrom fractions eluted with hexane-ethyl acetate (9:1)

Sources & evidence

ORD record
ord-8ceaeedd14014505b874f691e95a9e64
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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