Sodium Bicarbonate → HCID 23159707, compound

HRID 1174441Notes

Reaction equation

HRID 1174441 reaction equation
O[C:2]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH2:24][CH2:25][F:26])[CH2:7][CH2:6][CH:5]([CH:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH3:16])[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:14]([CH:11]1[CH2:10][CH2:9][CH:8]([CH:5]2[CH2:6][CH2:7][C:2]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23][CH2:24][CH2:25][F:26])=[CH:3][CH2:4]2)[CH2:13][CH2:12]1)[CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 87253079HCID 87253079, compound

Product 1

HCID 23159707HCID 23159707, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The crude 1-hydroxy-4-(4-propylcyclohexyl)cyclohexyl-2-fluoroethoxybenzene obtained in the first step was dissolved in toluene. p-Toluene sulfonic acid monohydrate was added and refluxed while heating for two hours under dewatering by using a Dean-Stark apparatus. The reaction mixture was poured into an aqueous saturated sodium hydrogen carbonate solution and extracted with toluene. The organic layer was washed with water and then with an aqueous saturated sodium chloride solution successively and, after dying over anhydrous magnesium sulfate, concentrated under a reduced pressure. The residue was purified by silica gel column chromatography to obtain 4-(4-propylcyclohexyl)cyclohexenyl-2-fluoroethoxybenzene.

Workup

  1. temperaturerefluxed
  2. temperaturewhile heating for two hours
  3. extractionextracted with toluene
  4. washThe organic layer was washed with water
  5. concentrationconcentrated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-06d2313894db4605ae5f1d62cecb49b9
Source dataset
uspto-grants-2010_11
Patent number
US07838087B2

Reaction notes

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