HCID 12788283, compound → HCID 70527478, compound

HRID 1660067Notes

Reaction equation

HRID 1660067 reaction equation
[CH3:1][C:2]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH:21]([CH2:22][CH:23]=[CH2:24])[CH2:20][CH2:19][CH:18]([OH:25])[CH2:17]2)=[C:12]([OH:26])[CH:11]=1)([CH3:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl.CCOCC>[CH3:9][C:2]([C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[C@H:21]([CH2:22][CH:23]=[CH2:24])[CH2:20][CH2:19][C:18](=[O:25])[CH2:17]2)=[C:12]([OH:26])[CH:11]=1)([CH3:1])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 12788283HCID 12788283, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 70527478HCID 70527478, compoundYield 9.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-4-(2-propenyl)cyclohexanol (2.15 g, 6.03 mmole) (mixture of isomers) in dichloromethane (15 ml) was added pyridinium chlorochromate (2.59 g, 12.1 mmole). The reaction mixture was stirred for 2 hours at room temperature, diluted with ether, diatomaceous earth added and the mixture filtered through magnesium sulfate. The evaporated filtrate was purified via column chromatography on 200 g of silica gel eluted with 20% ether-pentane to yield 250 mg of crude title compound. This was further purified via preparative layer chromatography on two 20 cm×20 cm×2 mm silica gel plates eluted twice with 20% ether-pentane to yield 200 mg (9.3%) of the title compound as an oil.

Workup

  1. additionadded
  2. filtrationthe mixture filtered through magnesium sulfate
  3. customThe evaporated filtrate was purified via column chromatography on 200 g of silica gel
  4. washeluted with 20% ether-pentane
  5. customto yield 250 mg of crude title compound
  6. customThis was further purified via preparative layer chromatography on two 20 cm×20 cm×2 mm silica gel plates
  7. washeluted twice with 20% ether-pentane

Sources & evidence

ORD record
ord-b73642a1c5ec47a3ba5286877d53630e
Source dataset
uspto-grants-1981_12
Patent number
US04306097

Reaction notes

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