Water → Phenyl 2-methylbenzoate

HRID 1361801Notes

Reaction equation

HRID 1361801 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[OH2:11]>C1COCC1>[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:11][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:3]=1)=[O:5]

Participants

4

Reactant 2

HCID 962WaterHCID 702762-Methylbenzoyl chloride

Product 1

HCID 576772Phenyl 2-methylbenzoateYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution (10 mL) of 2-methylbenzoyl chloride (4.16 mL) in THF was added dropwise to the reaction mixture, followed by stirring overnight at room temperature. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=9:1) to afford phenyl 2-methylbenzoate (2.88 g, 64%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-f1dd66c0566342aa8f5c9996746e381a
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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