Melilotic acid → HCID 22731894, compound

HRID 2083885Notes

Reaction equation

HRID 2083885 reaction equation
[C:1]1([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1CCC(O)=O.C1(Br)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O.CCCCCC.CCOC(C)=O>[C:1]1([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][CH2:15][C:16]([O:18][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 873Melilotic acidHCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 27644363-(2-phenoxyphenyl)propanoic Acid

Product 1

HCID 22731894HCID 22731894, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21226206Ethyl acetate hexaneSolvent2×

Procedure

3-(2-Phenyloxyphenyl)propionic Acid. 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-9ace9f1d9b2c4facbb2d2c8107525b9f
Source dataset
uspto-grants-2004_04
Patent number
US06716818B2

Reaction notes

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