Lithium Hydroxide → Fibric acid

HRID 1890777Notes

Reaction equation

HRID 1890777 reaction equation
[CH3:1][C:2]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:8])[C:3]([O:5]CC)=[O:4].[Li+].[OH-]>CO>[CH3:8][C:2]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:1])[C:3]([OH:5])=[O:4]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86476Deschloroclofibrate

Product 1

HCID 70343Fibric acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-2-phenoxypropanoic acid from Step A (0.05 mmol) in methanol (200 mL) was added aqueous LiOH (150 mL, 1 mol). The reaction mixture was refluxed for 3 hours. After removal of the solvent, the residue was extracted with ethyl acetate (50 mL×2). The aqueous layer was adjusted to pH=2 with concentrated HCl and extracted with ethyl acetate (200 mL×4). The combined extracts were washed with brine, dried with sodium sulfate and concentrated to give the titled compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.26˜7.30 (m, 2H), 7.06 (t, J=7.2 Hz 1H), 6.93-6.95 (m, 2H), 1.61 (s, 6H); LCMS (ESI+) m/z 181 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customAfter removal of the solvent
  3. extractionthe residue was extracted with ethyl acetate (50 mL×2)
  4. extractionextracted with ethyl acetate (200 mL×4)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9824762b85e14d78a224207887342b3a
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

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