Ethanol → Ethyl 7-oxo-7-phenylheptanoate

HRID 2250564Notes

Reaction equation

HRID 2250564 reaction equation
[C:1]([CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-][CH2:17][CH3:18].[Na+].C([OH:22])C>>[O:8]=[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][CH2:14][CH2:13][CH2:12][CH2:11][C:10]([O:15][CH2:17][CH3:18])=[O:22]

Participants

4

Reactant 3

HCID 702EthanolHCID 2756272-BenzoylcyclohexanoneHCID 2723922Sodium ethoxide

Product 1

HCID 11107694Ethyl 7-oxo-7-phenylheptanoate

Procedure

A mixture of 2-benzoylcyclohexanone (1.00 g), sodium ethoxide (404 mg) in ethanol (5 mL) was stirred for 3.5 hours at room temperature. The reaction was quenched by adding 1N hydrochloric acid (1 mL). The solvent was evaporated off, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated to give ethyl 7-oxo-7-phenylheptanoate as a brown oil (1.33 g).

Workup

  1. customThe reaction was quenched
  2. additionby adding 1N hydrochloric acid (1 mL)
  3. customThe solvent was evaporated off
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-49f99ca24a1e458e914af8312df96569
Source dataset
uspto-grants-2008_01
Patent number
US07317009B2

Reaction notes

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