Hydrochloric Acid → HCID 178455760, compound

HRID 1977013Notes

Reaction equation

HRID 1977013 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]([C@H:26]1[CH2:31][CH2:30][C@H:29]([C@H:32]2[CH2:37][CH2:36][C@H:35]([CH:38]=[CH:39][C@H:40]3[CH2:45][CH2:44][C@H:43]([CH2:46][CH2:47][CH2:48][C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[CH2:42][CH2:41]3)[CH2:34][CH2:33]2)[CH2:28][CH2:27]1)=[CH2:25]>O>[CH:24]([C@H:26]1[CH2:31][CH2:30][C@H:29]([C@H:32]2[CH2:33][CH2:34][C@H:35](/[CH:38]=[CH:39]/[C@H:40]3[CH2:45][CH2:44][C@H:43]([CH2:46][CH2:47][CH2:48][C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[CH2:42][CH2:41]3)[CH2:36][CH2:37]2)[CH2:28][CH2:27]1)=[CH2:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21863594Toluene ethanolHCID 23681562Benzenesulfinic acid, sodium salt, dihydrateHCID 178455761HCID 178455761, compound

Product 1

HCID 178455760HCID 178455760, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture prepared by adding 5.9 g (29.5 mmol) of sodium benzenesulfinate dihydrate, 5 ml of 6N hydrochloric acid, and 40 ml of mixed solvent of toluene/ethanol (1/1) to 6.1 g (14.5 mmol) of the crude 4-(trans-4-(2-(trans-4-(trans-4-vinylcyclohexyl)cyclohexyl)vinyl)cyclohexyl)propylbenzene was refluxed for 40 hours. Water in an amount of 30 ml was added to the reaction mixture, extracted with 150 ml of toluene, washed with water thrice, and then 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: heptane/toluene=95/5) to obtain 3.8 g of a crude (E)-4-(trans-4-(2-(trans-4-(trans-4-vinylcyclohexyl)cyclohexyl)-vinyl)cyclohexyl)propylbenzene. This product was recrystallized from a mixed solvent of ethanol/ethyl acetate to obtain 1.1 g of the subjective compound.

Workup

  1. customA mixture prepared
  2. temperaturewas refluxed for 40 hours
  3. extractionextracted with 150 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-c5cab404dc7c48a191c949dd935b9ed1
Source dataset
uspto-grants-2001_05
Patent number
US06231934B1

Reaction notes

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