Toluene → HCID 22384012, compound

HRID 1257945Notes

Reaction equation

HRID 1257945 reaction equation
C1(C)C=CC=CC=1.[CH2:8]([CH:11]1[CH2:20][CH2:19][CH:18]2[CH:13]([CH2:14][CH2:15][CH:16]([CH:21]3[CH2:30][CH2:29][C:24]4(OCC[O:25]4)[CH2:23][CH2:22]3)[CH2:17]2)[CH2:12]1)[CH2:9][CH3:10]>C(O)=O>[CH2:8]([CH:11]1[CH2:20][CH2:19][CH:18]2[CH:13]([CH2:14][CH2:15][CH:16]([CH:21]3[CH2:22][CH2:23][C:24](=[O:25])[CH2:29][CH2:30]3)[CH2:17]2)[CH2:12]1)[CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 1140TolueneHCID 22384143HCID 22384143, compound

Product 1

HCID 22384012HCID 22384012, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Sixth step: Toluene (300 ml) and formic acid (98%; 15 g) were added to 8-(6-propyldecahydronaphthalene-2-yl)-1,4-dioxaspiro[4.5]decane (27.9 g) obtained in the fifth step, and the mixture was stirred for 7 hours. After the reaction mixture had been cooled to room temperature, it was washed with aqueous sodium hydroxide solution (1M) and water, and dried over anhydrous magnesium sulfate. The toluene was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-heptane=1/9 by volume) to give 4-(6-propyldecahydronaphthalene-2-yl)cyclohexanone (24.1 g).

Workup

  1. customobtained in the fifth step
  2. washit was washed with aqueous sodium hydroxide solution (1M) and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe toluene was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-heptane=1/9 by volume)

Sources & evidence

ORD record
ord-a8beca4462d84a14b37313aefdf659d8
Source dataset
uspto-grants-2013_06
Patent number
US08465674B2

Reaction notes

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