Acetic Acid → 2-(4-Hexylphenyl)acetic acid

HRID 1504271Notes

Reaction equation

HRID 1504271 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10](C(=O)C)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:16]([OH:19])(=[O:18])[CH3:17].S(=O)(=O)(O)O>O>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([CH2:17][C:16]([OH:19])=[O:18])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 1234624-Hexylacetophenone

Product 1

HCID 20634302-(4-Hexylphenyl)acetic acidYield 66.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
150 °C

Procedure

12.0 g (39.3 mmol) of 1-(4-hexylphenyl)ethanone was dissolved in 23.6 g (393 mmol) of glacial acetic acid mixed with 4.95 g (275 mmol) of water and 5.79 g (58.9 mmol) of sulfuric acid and heated at 150° C. for 6.5 hours under reflux. After completion of the reaction, the reaction solution was diluted with 400 mL of water and extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate:hexane (1:20 to 1:4) as the eluent to give 5.74 g of the desired product as white crystals.

Workup

  1. temperatureunder reflux
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3b8086d24b7a41aa901a4dc2331f1003
Source dataset
uspto-grants-2015_12
Patent number
US09212348B2

Reaction notes

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