Sodium hydride → Ethyl 2-(3-undecylphenoxy)-3-oxopentanoate

HRID 1081649Notes

Reaction equation

HRID 1081649 reaction equation
[CH2:1]([C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[H-].[Na+].Cl[CH:22]([C:28](=[O:31])[CH2:29][CH3:30])[C:23]([O:25][CH2:26][CH3:27])=[O:24]>C1(C)C=CC=CC=1.O.C(O)(=O)C>[CH2:1]([C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=1)[O:18][CH:22]([C:28](=[O:31])[CH2:29][CH3:30])[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 12923424Ethyl 2-chloro-3-oxopentanoateHCID 232748073-Undecylphenol

Product 1

HCID 19955508Ethyl 2-(3-undecylphenoxy)-3-oxopentanoateYield 81.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 7.0 grams (0.028 mole) of 3-undecylphenol (prepared in Steps A-C of this Example) and 1.1 grams (0.028 mole) of 60% sodium hydride (in mineral oil) in 100 mL of toluene was stirred for about 20 minutes, and 4.2 grams (0.028 mole) of ethyl 2-chloro-3-oxopentanoate (prepared in Step D of this example) was added dropwise during about a 12 minute period. Upon completion of addition, the reaction mixture was heated to reflux, where it was stirred for about 6.5 hours. After this time, the reaction mixture was allowed to cool to ambient temperature, where it stood for about 16 hours. The reaction mixture was then taken up in 50 mL of water and 5 mL of acetic acid. The mixture was washed with an additional 50 mL of water and then with 25 mL of an aqueous solution saturated with sodium chloride. The organic layer was dried with sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 8.9 grams of ethyl 2-(3-undecylphenoxy)-3-oxopentanoate. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionwas added dropwise during about a 12 minute period
  2. additionUpon completion of addition
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux
  5. stirringwhere it was stirred for about 6.5 hours
  6. waitwhere it stood for about 16 hours
  7. washThe mixture was washed with an additional 50 mL of water
  8. dry with materialThe organic layer was dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f08a9417268e439da7bbe67b176fc5b5
Source dataset
uspto-grants-1996_12
Patent number
US05587379

Reaction notes

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