Potassium Carbonate → HCID 54033222, compound

HRID 1492827Notes

Reaction equation

HRID 1492827 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([OH:11])[CH:5]=1.Br[CH2:14][CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:5]=[C:6]([O:11][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=[C:8]([O:10][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzeneHCID 75076Methyl 3,5-Dihydroxybenzoate

Product 1

HCID 54033222HCID 54033222, compoundYield 74.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.68 g (0.01 mol) of 3,5-dihydroxybenzoic acid methyl ester, 3.4 mL (0.022 mol) of 3-bromopropylbenzene and 2.8 g (0.02 mol) of potassium carbonate in 50 mL of anhydrous DMF was stirred and heated at 100° for 18 hours. The solvent was removed at reduced pressure, the residue was acidified and the product was extracted with ethyl acetate. The dried extract was concentrated to dryness and the residue was purified by chromatography on 150 g of silica gel using 10 % ethyl acetate-hexane to give 3.0 g of 3,5-bis(3-phenylpropoxy)benzoic acid methyl ester as an oil. The nmr and mass spectra were consistent with the structure.

Workup

  1. temperatureheated at 100° for 18 hours
  2. customThe solvent was removed at reduced pressure
  3. extractionthe product was extracted with ethyl acetate
  4. extractionThe dried extract
  5. concentrationwas concentrated to dryness
  6. customthe residue was purified by chromatography on 150 g of silica gel using 10 % ethyl acetate-hexane

Sources & evidence

ORD record
ord-5a4e5cd7040b4f889d1d55ae3069cee9
Source dataset
uspto-grants-1994_12
Patent number
US05374772

Reaction notes

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