Ethanol → Ethyl 2-(4-hexylphenyl)acetate

HRID 244933Notes

Reaction equation

HRID 244933 reaction equation
[CH2:1]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].S(=O)(=O)(O)O.[CH2:22](O)[CH3:23]>>[CH2:1]([C:7]1[CH:8]=[CH:9][C:10]([CH2:13][C:14]([O:16][CH2:22][CH3:23])=[O:15])=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 20634302-(4-Hexylphenyl)acetic acid

Product 1

HCID 3703215Ethyl 2-(4-hexylphenyl)acetate

Conditions

Temperature
60 °C

Procedure

5.5 g (25 mmol) of 2-(4-hexylphenyl)acetic acid was dissolved in 11 mL of ethanol and mixed with 1.1 g (11.2 mmol) of sulfuric acid and stirred at 60° C. for 1 hour. The reaction was quenched with cold saturated aqueous sodium carbonate (100 ml), and the reaction solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give 5.68 g of the desired product as a pale yellow oil.

Workup

  1. customThe reaction was quenched with cold saturated aqueous sodium carbonate (100 ml)
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1106d78e57ec404380b319f778b70f45
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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