Ethanol → HCID 17989170, compound

HRID 420618Notes

Reaction equation

HRID 420618 reaction equation
[F:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]([C:9]([CH3:17])([CH3:16])[CH2:10][C:11](=[O:15])[C:12]([OH:14])=[O:13])[CH:5]=[CH:6][C:7]=1[CH3:8].S(=O)(=O)(O)O.[CH2:25](O)[CH3:26]>>[CH2:25]([O:13][C:12](=[O:14])[C:11](=[O:15])[CH2:10][C:9]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([F:1])[C:3]=1[O:18][CH3:19])([CH3:17])[CH3:16])[CH3:26]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 17989292HCID 17989292, compound

Product 1

HCID 17989170HCID 17989170, compoundYield 83.7%

Procedure

6.04 g (22.52 mmol) of 4-(3-fluoro-2-methoxy-4-methylphenyl)-4-methyl-2-oxo-pentanoic acid is dissolved in 140 ml of ethanol, mixed with 2.5 ml of sulfuric acid, and refluxed for six hours. The ethanol is drawn off in a rotary evaporator, and the residue is carefully mixed with 300 ml of saturated sodium bicarbonate solution. It is extracted three times with ethyl acetate. The combined organic extracts are washed once with saturated sodium bicarbonate solution and once with brine. After drying, and after the desiccant is filtered off and the solvent is spun in, the residue is chromatographed on silica gel (mobile solvent ethyl acetate/hexane). 5.58 g (83.7%) of the desired compound is isolated.

Workup

  1. temperaturerefluxed for six hours
  2. customThe ethanol is drawn off in a rotary evaporator
  3. additionthe residue is carefully mixed with 300 ml of saturated sodium bicarbonate solution
  4. extractionIt is extracted three times with ethyl acetate
  5. washThe combined organic extracts are washed once with saturated sodium bicarbonate solution and once with brine
  6. customAfter drying
  7. filtrationafter the desiccant is filtered off
  8. customis chromatographed on silica gel (mobile solvent ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b8f10def836b40faa30a029499446d2a
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

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