Ethanol → Ethyl 4-oxo-4-phenylbutyrate

HRID 2250563Notes

Reaction equation

HRID 2250563 reaction equation
[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:14](O)[CH3:15].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.CN(C)C=O>[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][CH2:4][C:5]([O:7][CH2:14][CH3:15])=[O:6]

Participants

6

Reactant 3

HCID 702EthanolHCID 728713-Benzoylpropionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 80451Ethyl 4-oxo-4-phenylbutyrateYield 72.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-oxo-4-phenylbutanoic acid (5.00 g), ethanol (2.59 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6.46 g), and 4-(dimethylamino)pyridine (171 mg) in N,N-dimethylformamide (25 mL) was stirred for 1.5 hours at room temperature. The mixture was partitioned between ethyl acetate (100 mL) and 1N hydrochloric acid (75 mL), and the organic layer was washed with water (75×3 mL), saturated sodium bicarbonate (75 mL), and brine (75 mL), dried over magnesium sulfate, and evaporated to give ethyl 4-oxo-4-phenylbutanoate as a colorless oil (4.19 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate (100 mL) and 1N hydrochloric acid (75 mL)
  2. washthe organic layer was washed with water (75×3 mL), saturated sodium bicarbonate (75 mL), and brine (75 mL)
  3. dry with materialdried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-21258069a84b44b88430e689121f18e4
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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