Ethanol → HCID 17989304, compound

HRID 420629Notes

Reaction equation

HRID 420629 reaction equation
[Cl: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]([Cl:1])[C:3]=1[O:18][CH3:19])([CH3:17])[CH3:16])[CH3:26]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 17989150HCID 17989150, compound

Product 1

HCID 17989304HCID 17989304, compoundYield 81.6%

Procedure

5.37 g (18.86 mmol) of 4-(3-chloro-2-methoxy-4-methylphenyl)-4-methyl-2-oxo-pentanoic acid is dissolved in 112 ml of ethanol, mixed with 2 ml of concentrated sulfuric acid and refluxed for five hours. The ethanol is drawn off in a rotary evaporator, and the residue is carefully mixed with saturated sodium bicarbonate solution after 50 ml of water is added. It is extracted twice with ethyl acetate. The combined organic extracts are washed with water and 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). 4.81 g (81.6%) of the desired compound is isolated.

Workup

  1. temperaturerefluxed for five hours
  2. customThe ethanol is drawn off in a rotary evaporator
  3. additionthe residue is carefully mixed with saturated sodium bicarbonate solution after 50 ml of water
  4. additionis added
  5. extractionIt is extracted twice with ethyl acetate
  6. washThe combined organic extracts are washed with water and with brine
  7. customAfter drying
  8. filtrationafter the desiccant is filtered off
  9. customis chromatographed on silica gel (mobile solvent ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e57c3690c8e744ee9e11b920209767e6
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

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