Melilotic acid → HCID 22731894, compound

HRID 276753Notes

Reaction equation

HRID 276753 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([OH:12])=[O:11].[C:13]1(Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.CCCCCC.CCOC(C)=O>[C:13]1([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][CH2:9][C:10]([O:12][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:11])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 873Melilotic acidHCID 7961BromobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 22731894HCID 22731894, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21226206Ethyl acetate hexaneSolvent2×

Procedure

A mixture of 3-(2-hydroxyphenyl)propionic acid (0.57 g, 3.4 mmol), phenylbromide (0.4 ml, 3.37 mmol), and K2CO3 (2.5 g) in acetone (10 ml) was stirred at room temperature for 2 days. The mixture was diluted with 1:1 hexane/EtOAc (100 ml), washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by chromatography (5:1 then 4:1 hexane/EtOAc) to yield phenyl 3-(2-phenyloxyphenyl)propionate (0.45 g, 1.30 mmol, 77%).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by chromatography (5:1

Sources & evidence

ORD record
ord-0e056fb50a914e7aab1455c7f22b1817
Source dataset
uspto-grants-2002_03
Patent number
US06355618B1

Reaction notes

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