8-(2-Chlorophenylmethylene)-1,4-dioxaspiro[4.5]decane → 8-(2-Chlorophenylmethyl)-1,4-dioxaspiro[4.5]decane

HRID 727161Notes

Reaction equation

HRID 727161 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[C:9]1[CH2:18][CH2:17][C:12]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:11][CH2:10]1>C(O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]1[CH2:18][CH2:17][C:12]2([O:13][CH2:14][CH2:15][O:16]2)[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 197052048-(2-Chlorophenylmethylene)-1,4-dioxaspiro[4.5]decane

Product 1

HCID 197052768-(2-Chlorophenylmethyl)-1,4-dioxaspiro[4.5]decaneYield 72.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 6.9 grams (0.026 mole) of 8-(2-chlorophenylmethylene)-1,4-dioxaspiro[4.5]decane in about 50 mL of ethanol and 0.4 gram (catalyst) of 10% palladium on charcoal were placed in a hydrogenation bottle and hydrogenated using a Parr hydrogenation apparatus. Upon the theoretical uptake of hydrogen, the reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography using silica gel. Elution was accomplished using 33% ethyl acetate in hexane. The product-containing fractions were combined and concentrated under reduced pressure, yielding 5.0 grams of 8-(2-chlorophenylmethyl)-1,4-dioxaspiro[4.5]decane. The NMR spectrum was consistent with the proposed structure.

Workup

  1. filtrationUpon the theoretical uptake of hydrogen, the reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under reduced pressure to a residue
  4. washElution
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ff0de943fd714e2185f8a23133b7b34b
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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