Acetone → 2-[2-(Naphthalenyloxy) ethoxy]benzoic acid methyl ester

HRID 1492833Notes

Reaction equation

HRID 1492833 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](O)[CH:7]=[C:6](O)[CH:5]=1.BrCCO[C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1.[I-].[Na+].[C:29](=[O:32])([O-])[O-].[K+].[K+].C[C:36](C)=[O:37]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:37][CH2:36][CH2:29][O:32][C:20]1[C:19]2[C:24](=[CH:25][CH:26]=[CH:17][CH:18]=2)[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 5

HCID 180AcetoneHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 75076Methyl 3,5-DihydroxybenzoateHCID 6406922-(2-Bromoethoxy)naphthalene

Product 1

HCID 570358912-[2-(Naphthalenyloxy) ethoxy]benzoic acid methyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.90 g (5.3 mmol) of 3,5-dihydroxybenzoic acid methyl ester, 2.95 g (11.8 mmol) of 2-(2-bromoethoxy)naphthalene, 1.8 g (11.8 mmol) of sodium iodide and 3 g (21.7 mmol) of potassium carbonate in 80 mL of acetone and 25 mL of DMF was stirred at reflux for 40 hours. The solvents were removed at reduced pressure, water was added to the residue and the product was extracted with ethyl acetate. The dried extract was concentrated to a solid which was recrystallized from ethyl acetate to give 1.6 g (59% yield, mp 132°-137°) of 3,5-bis[2-[2-(naphthalenyloxy) ethoxy]benzoic acid methyl ester.

Workup

  1. temperatureat reflux for 40 hours
  2. customThe solvents were removed at reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe product was extracted with ethyl acetate
  5. extractionThe dried extract
  6. concentrationwas concentrated to a solid which
  7. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2658393421df4443a480fab7a1cabaf9
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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