Potassium Carbonate → HCID 19801964, compound

HRID 1646272Notes

Reaction equation

HRID 1646272 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.Cl[CH2:16][CH2:17][CH2:18][OH:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:19][CH2:18][CH2:17][CH2:16][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:14])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 12785115Ethyl 2-(4-hydroxyphenyl)propanoate

Product 1

HCID 19801964HCID 19801964, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 2-[4-hydroxyphenyl]propionate [20 mmole] was combined with 3-chloropropanol [22 mmole] and potassium carbonate [24 mmole] in acetone [100 ml], then refluxed for 18 hours. After removal of the acetone under reduced pressure, the reaction mixture was extracted with 1N sodium hydroxide solution to remove acidic components. These were chromatographed on silica gel/toluene to isolate the product, 2-[4-(3-hydroxypropoxy)phenyl]propionic acid, as an amorphous solid. Mass spectral, proton nuclear magnetic resonance, and elemental analysis data are consistent with the assigned structure. Additional product was obtained by basic hydrolysis of the neutral fraction, followed by silica gel/toluene chromatography.

Workup

  1. temperaturerefluxed for 18 hours
  2. customAfter removal of the acetone under reduced pressure
  3. extractionthe reaction mixture was extracted with 1N sodium hydroxide solution
  4. customto remove acidic components
  5. customThese were chromatographed on silica gel/toluene

Sources & evidence

ORD record
ord-ce01b852beff4acebc2cb523fa922f0e
Source dataset
uspto-grants-1993_01
Patent number
US05179124

Reaction notes

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