Water → HCID 117666152, compound

HRID 523350Notes

Reaction equation

HRID 523350 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8](=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:4][CH2:3]1.[CH3:15][C@H:16]([CH2:20][CH2:21][CH:22]=[C:23](C)[CH3:24])[CH2:17]CO.O(C)[Na].O>C1CCCCC1.CCOCC>[CH3:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:8](=[O:14])[C:9]([O:11][CH2:12][CH2:13][C@H:23]([CH3:24])[CH2:22][CH2:21][CH:20]=[C:16]([CH3:17])[CH3:15])=[O:10])[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 101977D-CitronellolHCID 55269669HCID 55269669, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 117666152HCID 117666152, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8078CyclohexaneSolvent

Procedure

A solution of ethyl 2-(4-methylcyclohexyl)-2-oxoacetate (5.0 g, 25 mmol), of (R)-3,7-dimethyl-6-octenol (4.74 g, 30 mmol) and NaOCH3 (0.5 ml, 30% in methanol) in cyclohexane (50 ml) was heated with a water separator under reflux for 2 days. After cooling to room temperature, ether was added and the organic phase washed with a saturated solution of NaCl, dried (Na2SO4), filtered and concentrated. Column chromatography (SiO2, heptane/ether 7:3 and heptane/ether 95:5) gave 1.16 g (15%) of the pure product a colorless oil as a mixture of cis/trans isomers (ca. 1:3).

Workup

  1. temperatureunder reflux for 2 days
  2. washthe organic phase washed with a saturated solution of NaCl
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3bee04d3bf534a239fcec98a3a745335
Source dataset
uspto-grants-2016_05
Patent number
US09334464B2

Reaction notes

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