Ethyl benzoylformate → HCID 89601146, compound

HRID 523345Notes

Reaction equation

HRID 523345 reaction equation
[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:14]/[C:15](/[CH2:19][CH2:20][CH:21]=[C:22](C)[CH3:23])=[CH:16]\CO.O(C)[Na]>C1CCCCC1.CCOCC>[O:1]=[C:2]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([O:5][CH2:6]/[CH:7]=[C:22](\[CH3:23])/[CH2:21][CH2:20][CH:19]=[C:15]([CH3:16])[CH3:14])=[O:4]

Participants

6

Reactant 3

HCID 15349Ethyl benzoylformateHCID 637566GeraniolHCID 178418582HCID 178418582, compound

Product 1

HCID 89601146HCID 89601146, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8078CyclohexaneSolvent

Procedure

A solution of ethyl 2-oxo-2-phenylacetate (17.6 g, 99 mmol), (E)-3,7-dimethyl-2,6-octadienol (18.5 g, 120 mmol) and NaOCH3 (30% in methanol, 1.5 ml) in cyclohexane (170 ml) was heated under reflux for 72 h. After cooling to room temperature the reaction mixture was taken up in ether, washed with water (pH≈7), dried (Na2SO4), filtered and concentrated. Column chromatography (SiO2, heptane/ether 8:2) afforded 14.5 g (52%) of a slightly yellow oil.

Workup

  1. temperatureunder reflux for 72 h
  2. washwashed with water (pH≈7)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customColumn chromatography (SiO2, heptane/ether 8:2) afforded 14.5 g (52%) of a slightly yellow oil

Sources & evidence

ORD record
ord-c406151ba91244efa4065e28e3e8a86d
Source dataset
uspto-grants-2016_05
Patent number
US09334464B2

Reaction notes

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