Ethanol → ethyl 5-phenylpentanoate

HRID 894375Notes

Reaction equation

HRID 894375 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:19][CH3:20])=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 16757Benzenepentanoic acid

Product 1

HCID 234289ethyl 5-phenylpentanoateYield 97.5%

Procedure

250 g (1.4 mols) of 5-phenylvaleric acid are dissolved in 450 ml of absolute ethanol. 114 ml of concentrated sulphuric acid are added to the clear colourless solution and the reaction mixture is refluxed for 48 hours. The reaction mixture, which initially is two-phase, becomes almost homogeneous and separates into two phases again on cooling. The cold two-phase reaction mixture is poured onto diethyl ether and about 1 kg of ice. The aqueous phase is extracted with ether twice more. The ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution. The combined ether phases are dried over MgSO4 and the solvent is removed on a rotary evaporator. After drying under a high vacuum at room temperature, 281.7 g of a colourless oil (97.5% of theory) are obtained.

Workup

  1. temperaturethe reaction mixture is refluxed for 48 hours
  2. temperatureon cooling
  3. customThe cold two-phase reaction mixture
  4. extractionThe aqueous phase is extracted with ether twice more
  5. washThe ether phases are washed twice with 2 N sodium carbonate solution and twice with NaCl solution
  6. dry with materialThe combined ether phases are dried over MgSO4
  7. customthe solvent is removed on a rotary evaporator
  8. customAfter drying under a high vacuum at room temperature

Sources & evidence

ORD record
ord-89ff7a075d54477aa5f6200a029432e0
Source dataset
uspto-grants-1981_08
Patent number
US04283509

Reaction notes

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