Hydrochloric Acid → HCID 178455746, compound

HRID 1977012Notes

Reaction equation

HRID 1977012 reaction equation
O.O.C1(S([O-])=O)C=CC=CC=1.[Na+].Cl.C1(C)C=CC=CC=1.C(O)C.[CH:24]([CH:26]1[CH2:31][CH2:30][CH:29]([CH:32]=[CH:33][C@H:34]2[CH2:39][CH2:38][C@H:37]([C:40]3[CH:45]=[CH:44][C:43]([C:46]4[CH:51]=[CH:50][C:49]([CH2:52][CH2:53][CH2:54][CH3:55])=[CH:48][CH:47]=4)=[CH:42][CH:41]=3)[CH2:36][CH2:35]2)[CH2:28][CH2:27]1)=[CH2:25]>O>[CH:24]([C@H:26]1[CH2:27][CH2:28][C@H:29](/[CH:32]=[CH:33]/[C@H:34]2[CH2:35][CH2:36][C@H:37]([C:40]3[CH:41]=[CH:42][C:43]([C:46]4[CH:51]=[CH:50][C:49]([CH2:52][CH2:53][CH2:54][CH3:55])=[CH:48][CH:47]=4)=[CH:44][CH:45]=3)[CH2:38][CH2:39]2)[CH2:30][CH2:31]1)=[CH2:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21863594Toluene ethanolHCID 23681562Benzenesulfinic acid, sodium salt, dihydrateHCID 178436257HCID 178436257, compound

Product 1

HCID 178455746HCID 178455746, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture prepared by adding 3.3 g (16.5 mmol) of sodium benzenesulfinate dihydrate, 2.7 ml of 6N hydrochloric acid, and 25 ml of mixed solvent of toluene/ethanol (1/1) to 3.5 g (8.3 mmol) of the crude 4-(trans-4-(2-(4-vinylcyclohexyl)vinyl)cyclohexyl)-4′-butylbiphenyl was refluxed for 95 hours. Water in an amount of 50 ml was added to the reaction mixture, and the mixture was extracted with 100 ml of toluene, washed with water thrice, and dried over anhydrous magnesium sulfate. The solvent was distilled off under a reduced pressure, and the residue was subjected to silica gel column chromatography (eluent: toluene/heptane=1/9) to obtain 2.8 g of a crude (E)-4-(trans-4-(2-(trans-4-vinylcyclohexyl)vinyl)cyclohexyl)-4′-butylbiphenyl. This product was recrystallized from a mixed solvent of ethanol/ethyl acetate to obtain 0.7 g of the subjective compound.

Workup

  1. customA mixture prepared
  2. temperaturewas refluxed for 95 hours
  3. extractionthe mixture was extracted with 100 ml of toluene
  4. washwashed with water thrice
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under a reduced pressure

Sources & evidence

ORD record
ord-c602f9ef9990488582353e32eb5af3cc
Source dataset
uspto-grants-2001_05
Patent number
US06231934B1

Reaction notes

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