Sodium Iodide → 2-[3-Carboxypropyloxy]-dibenzofuran

HRID 128512Notes

Reaction equation

HRID 128512 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[CH2:15]([C:17](Br)(CC)[C:18]([O-:20])=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(=O)CC>[C:18]([CH2:17][CH2:15][CH2:16][O:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1)([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 665872-DibenzofuranolHCID 21584491Ethylbromobutyrate

Product 1

HCID 194336012-[3-Carboxypropyloxy]-dibenzofuran

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2-Hydroxydibenzofuran (0.5 gm, 2.7 mmol), ethylbromobutyrate (0.78 mL, 5.4 mmol), potassium carbonate (1.1 gm, 8.1 mmol), and sodium iodide (10 mg) were combined in 2-butanone (15 mL). The reaction was refluxed until complete, then the reaction filtered and the solvent removed under reduced pressure. The residue was taken up in 6M aqueous KOH/methanol, 1:1. After the hydrolysis was complete the reaction was acidified to pH 3 and the product extracted with ethyl acetate. The residue was purified by column chromatography (silica gel, ethyl acetate/hexanes/acetic acid, 10:30:60:0.5). The yield was 0.52 gm of product. Mass spectrum: DCI/NH3, (m+H)+ @ m/z 271, (m+NH4)+ @ m/z 288, (m+NH4 ·NH3)+ @ m/z 305.

Workup

  1. temperatureThe reaction was refluxed until complete, then the reaction
  2. filtrationfiltered
  3. customthe solvent removed under reduced pressure
  4. extractionthe product extracted with ethyl acetate
  5. customThe residue was purified by column chromatography (silica gel, ethyl acetate/hexanes/acetic acid, 10:30:60:0.5)

Sources & evidence

ORD record
ord-9f0b58938871469caa0115f86ab6fdaa
Source dataset
uspto-grants-1995_11
Patent number
US05464746

Reaction notes

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