HCID 10589340, compound → 3-(3-METHOXY-PHENYL)-2-METHYL-PROPIONIC ACID

HRID 323777Notes

Reaction equation

HRID 323777 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:3]=1[CH2:4][CH:5]([CH2:9]C)[C:6]([OH:8])=[O:7]>O>[CH3:16][O:15][C:12]1[CH:11]=[C:3]([CH2:4][CH:5]([CH3:9])[C:6]([OH:8])=[O:7])[CH:2]=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 10589340HCID 10589340, compound

Product 1

HCID 105839593-(3-METHOXY-PHENYL)-2-METHYL-PROPIONIC ACIDYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the butyric acid (4c, 51.6 g) and polyphosphoric acid (511 g) was heated at 100° C. for 2.5 hours. The mixture was poured into water (1 L) and extracted with AcOEt. The combined extracts were washed with water, 5% sodium bicarbonate solution and brine, dried over MgSO4 and filtered. After removing the solvent under reduced pressure, the residue was chromatographed on silica gel eluting with hexane:AcOEt (4:1 to 1:2) to give the titled compound (30.0 g).

Workup

  1. extractionextracted with AcOEt
  2. washThe combined extracts were washed with water, 5% sodium bicarbonate solution and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customAfter removing the solvent under reduced pressure
  6. customthe residue was chromatographed on silica gel eluting with hexane:AcOEt (4:1 to 1:2)

Sources & evidence

ORD record
ord-740c88a0fec443359a0f5fae316a478b
Source dataset
uspto-grants-2001_04
Patent number
US06214876B1

Reaction notes

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