Sodium Iodide → HCID 131716450, compound

HRID 2108235Notes

Reaction equation

HRID 2108235 reaction equation
BrCCCCCC(C1C=CC2C(=CC(OC)=C(OC)C=2)C=1)=O.[C:23]1([CH2:29][O:30][C:31](=[O:43])[C:32]2[CH:37]=[CH:36][C:35](O)=[C:34]([CH2:39][CH2:40][CH3:41])[C:33]=2O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O.CN(C)C=O>[C:23]1([CH2:29][O:30][C:31](=[O:43])[C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH2:39][CH2:40][CH3:41])[CH:33]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14986292HCID 14986292, compoundHCID 15107348HCID 15107348, compound

Product 1

HCID 131716450HCID 131716450, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7.60 g (0.021 mole) of 6-bromo-(6,7-dimethoxy-2-naphthalenyl)-1-hexanone, 5.96 g (0.021 mole) of 2,4-dihydroxy-3-propylbenzoic acid phenylmethyl ester, 5.75 g (0.042 mole) of potassium carbonate and 3.20 g (0.021 mole) of sodium iodide in 100 mL of acetone and 25 mL of dimethylformamide was stirred at reflux for 26 hours. The solvents were removed under reduced pressure and the crude product was purified by HPLC using 2% ethyl acetate-toluene, to give 8.14 g (69% yield) of 2-hydroxy-4-[[6,7-dimethoxy-2-naphthalenyl)-6-oxohexyl]oxy]-3-propylbenzoic acid phenylmethyl ester.

Workup

  1. temperatureat reflux for 26 hours
  2. customThe solvents were removed under reduced pressure
  3. customthe crude product was purified by HPLC

Sources & evidence

ORD record
ord-39d9ed8f37424a3c966be7cc2239ea77
Source dataset
uspto-grants-1990_06
Patent number
US04937371

Reaction notes

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