Ethanol → Ethyl 4-oxo-4-phenylbutyrate

HRID 860421Notes

Reaction equation

HRID 860421 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-8d92550510594bcfb234d56a63a8b99f
Source dataset
uspto-grants-2006_12
Patent number
US07153854B2

Reaction notes

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