P-Cymene → HCID 21568779, compound

HRID 1579551Notes

Reaction equation

HRID 1579551 reaction equation
[CH3:1][CH:2]([C:10]1[CH:11]=[C:12]([OH:26])[C:13]2[CH:14]([CH3:25])[C:15]3[CH2:16][CH2:17][CH:18]([CH3:24])[CH2:19][C:20]=3[O:21][C:22]=2[CH:23]=1)[CH:3]([CH3:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].CC1C=CC(C(C)C)=CC=1>[Pd].C(Cl)(Cl)Cl>[CH3:1][CH:2]([C:10]1[CH:11]=[C:12]([OH:26])[C:13]2[CH:14]([CH3:25])[C:15]3[C:20]([O:21][C:22]=2[CH:23]=1)=[CH:19][C:18]([CH3:24])=[CH:17][CH:16]=3)[CH:3]([CH3:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 7463P-Cymene2×HCID 21568780HCID 21568780, compound

Product 1

HCID 21568779HCID 21568779, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 1.7 g. of 3-(1,2-dimethylheptyl)-5,6,7,8-tetrahydro-1-hydroxy-6,9-dimethylxanthene in 70 ml. of p-cymene is added dropwise over one hour to a stirred suspension of 0.56 g. of 10% palladium-on-carbon in 70 ml. of refluxing p-cymene under a nitrogen atmosphere. The reaction mixture is refluxed for four hours, cooled and chloroform is added. The mixture is filtered and the filtrate is concentrated in vacuo to give a residue which is chromatographed on silica gel with 1:1 chloroform-cyclohexane as eluant to give the title compound, b.p. 208°-210° (0.004 mm.).

Workup

  1. temperatureThe reaction mixture is refluxed for four hours
  2. temperaturecooled
  3. filtrationThe mixture is filtered
  4. concentrationthe filtrate is concentrated in vacuo
  5. customto give a residue which
  6. customis chromatographed on silica gel with 1:1 chloroform-cyclohexane as eluant

Sources & evidence

ORD record
ord-266065bdc7b14bf59ae8260d32666d5e
Source dataset
uspto-grants-1976_01
Patent number
US03931232

Reaction notes

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