Hydrochloric Acid → HCID 178448016, compound

HRID 2081520Notes

Reaction equation

HRID 2081520 reaction equation
[CH:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=3)[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)=[CH:2][CH3:3].Cl.C1(S([O-])=O)C=CC=CC=1.[Na+].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH:1](/[C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:11][CH2:12][C@H:13]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[C:18]([F:23])[CH:17]=3)[CH2:14][CH2:15]2)[CH2:6][CH2:5]1)=[CH:2]\[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723840Benzenesulfinic acid, sodium saltHCID 178448017HCID 178448017, compound

Product 1

HCID 178448016HCID 178448016, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.303 g of the obtained 1-[trans-4-(trans-4-propenylcyclohexyl)cyclohexyl]-3, 4-difluorobenzene, 5 ml of toluene, 0.31 ml of 3N hydrochloric acid and 45 mg of sodium benzenesulfinate was stirred at 60°-65° C. for 3 hours. Subsequently, the reaction mixture was cooled to room temperature, poured on to 20 ml of 10% sodium hydrogencarbonate solution, and extracted with diethyl ether. The organic phases were washed with water, dried over sodium sulfate, and concentrated. Chromatographic purification of the crude product (0.314 g with an E/Z ratio of 83:16) with hexane/ethyl acetate (vol. 98:2) on silica gel treated with silver nitrate, and subsequent recrystallization from diethyl ether/methanol yielded 0.126 g of 1-[trans-4-(trans-4-(1E-propenyl)cyclohexyl]-cyclohexyl]-3,4-difluorbenzene as colorless crystals with m.p. (C-S ) 49.0° C., S -N 65.6° C., cl.p. (N-I) 159.7° C.; Δε (149° C)=3.22.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phases were washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customChromatographic purification of the crude product (0.314 g with an E/Z ratio of 83:16) with hexane/ethyl acetate (vol. 98:2) on silica gel
  6. additiontreated with silver nitrate, and subsequent recrystallization from diethyl ether/methanol

Sources & evidence

ORD record
ord-d9de038ed7df4f25a5bbe80d82ee6f41
Source dataset
uspto-grants-1993_02
Patent number
US05185098

Reaction notes

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