Ethanol → Ethyl 4-phenyl butyrate

HRID 1417899Notes

Reaction equation

HRID 1417899 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH2:18](O)[CH3:19]>>[CH2:18]([O:11][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 47754-Phenylbutyric Acid

Product 1

HCID 61452Ethyl 4-phenyl butyrateYield 97%

Procedure

A solution of 4-phenylbutyric acid (50.0 g, 0.3 mol) in ethanol (140 mL) with concentrated sulfuric acid (0.53 mL) was stirred at reflux over 5 hours. The cooled solution was poured into ice water and extracted with ethyl acetate. The combined organic layers were backwashed with brine, dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure to give 4-phenylbutyric acid ethyl ester (56.07 g, 0.29 mol, 97%) as a yellow liquid. 1H NMR (CDCl3) d 7.3-7.1 (m, 5H), 4.1 (q, 2H, J=7.1 Hz), 2.7 (t, 2H, J=7.7 Hz), 2.3 (t, 2H, J=7.5 Hz), 1.95 (quintet, 2H, J=7.5 Hz), 1.25 (t, 3H, J=7.1 Hz).

Workup

  1. temperatureat reflux over 5 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-59c1bdb154d54039a867a2a73a466ff5
Source dataset
uspto-grants-1999_03
Patent number
US05879657

Reaction notes

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