Toluene → HCID 66781461, compound

HRID 1095248Notes

Reaction equation

HRID 1095248 reaction equation
[CH2:1]([O:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3(O)[CH2:21][CH2:20][CH:19]([CH:22]4[CH2:31][CH2:30][C:25]5([O:29][CH2:28][CH2:27][O:26]5)[CH2:24][CH2:23]4)[CH2:18][CH2:17]3)=[C:12]([F:33])[CH:11]=2)[CH2:6][CH2:5]1)[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH2:1]([O:3][CH:4]1[CH2:5][CH2:6][CH:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH2:21][CH2:20][CH:19]([CH:22]4[CH2:23][CH2:24][C:25]5([O:26][CH2:27][CH2:28][O:29]5)[CH2:30][CH2:31]4)[CH2:18][CH:17]=3)=[C:12]([F:33])[CH:11]=2)[CH2:8][CH2:9]1)[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 66781645HCID 66781645, compound

Product 1

HCID 66781461HCID 66781461, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

The compound (23) (72.9 g), p-toluenesulfonic acid (2.19 g) and toluene (350 ml) were mixed, and the mixture was heated under reflux for 1.5 hours while water being distilled was removed. The reaction mixture was cooled to 30° C., and then water (700 ml) and toluene (900 ml) were added and mixed to it. The mixture was then allowed to stand until it had separated into two phases, the organic and aqueous phases, and an extractive operation to an organic phase was carried out. The organic phase was fractionated, and washed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water, and then dried over anhydrous magnesium sulfate. Then the solvent of the solution was distilled off under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using a mixed solvent of toluene and ethyl acetate (toluene:ethyl acetate=7:3 by volume) as an eluent and silica gel as a stationary phase powder, and further purified by means of recrystallization from heptane, and dried, giving 39.4 g of 8-(4-(4-(4-ethoxycyclohexyl)-2-fluorophenyl)cyclohex-3-enyl)-1,4-dioxaspiro[4,5]decane (24). The yield based on the compound (No. 22) was 78.8%.

Workup

  1. temperaturethe mixture was heated
  2. distillationdistilled
  3. customwas removed
  4. additionwater (700 ml) and toluene (900 ml) were added
  5. additionmixed to it
  6. customhad separated into two phases
  7. washwashed sequentially with a saturated aqueous solution of sodium hydrogencarbonate and water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThen the solvent of the solution was distilled off under reduced pressure
  10. customthe residue was purified with a fractional operation by means of column chromatography
  11. customsilica gel as a stationary phase powder, and further purified by means of recrystallization from heptane
  12. customdried

Sources & evidence

ORD record
ord-66e2c203736044eea315b5661c64f8e7
Source dataset
uspto-grants-2012_03
Patent number
US08137583B2

Reaction notes

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