3-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one → (+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanone

HRID 2307101Notes

Reaction equation

HRID 2307101 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[C:15]1[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH:16]=1.[H][H]>[Pd].C(O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:8]=[CH:7][C:6]=1[CH:15]1[CH2:20][CH2:19][CH2:18][C:17](=[O:21])[CH2:16]1

Participants

5

Reactant 2

HCID 121351713-[2,4-Bis(methoxymethoxy)phenyl]-2-cyclohexen-1-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 22337753(+/-)-3-[2,4-Bis(methoxymethoxy)phenyl]cyclohexanoneYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 3-[2,4-bis(methoxymethoxy)phenyl]-2-cyclohexen-1-one (300 m g) and palladium catalyst (50 mg, 10% palladium on carbon) in ethanol was stirred at ambient temperature under 1 atmosphere of hydrogen. After 16 hr, the mixture was filtered through celite and the filtrate was evaporated in vacuo. The product was dissolved in dichloromethane (15 ml). Celite and pyridinium chlorochromate (430 mg) were added and the mixture was stirred at room temperature. After 3 hr, the mixture was filtered through a pad of silica and eluted with petroleum ether/ethyl acetate (10:3, v/v), then purified by flash column chromatography (SiO2, petroleum ether/ethyl acetate 4:1 v/v) to furnish the title compound as an oil (200 mg, 70%). δH(CDCl3) 1.7-1.9 (2H, overlapping m), 2.05 (1H, m), 2.15 (1H, m), 2.35-2.60 (4H, overlapping m), 3.37 (1H, m), 3.490 (3H, s), 3.492 (3H, s), 5.15 (2H, s), 5.20 (2H, s), 6.70 (1H, dd), 6.82 (1H, d), 7.09 (1H, d).

Workup

  1. filtrationthe mixture was filtered through celite
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe product was dissolved in dichloromethane (15 ml)
  4. additionCelite and pyridinium chlorochromate (430 mg) were added
  5. waitAfter 3 hr
  6. filtrationthe mixture was filtered through a pad of silica
  7. washeluted with petroleum ether/ethyl acetate (10:3
  8. customv/v), then purified by flash column chromatography (SiO2, petroleum ether/ethyl acetate 4:1 v/v)

Sources & evidence

ORD record
ord-2f23dba86d9d4c59abf3c252295b12f7
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

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