Hydrochloric Acid → Pentacyclo[19.3.1.1~3,7~.1~9,13~.1~15,19~]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene

HRID 1756696Notes

Reaction equation

HRID 1756696 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].Cl.[C:6]1([CH3:12])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[CH2:12]1[C:10]2=[CH:11][C:6](=[CH:7][CH:8]=[CH:9]2)[CH2:12][C:10]2=[CH:11][C:6](=[CH:7][CH:8]=[CH:9]2)[CH2:12][C:8]2=[CH:9][CH:10]=[CH:11][C:6](=[CH:7]2)[CH2:12][C:8]2=[CH:9][CH:10]=[CH:11][C:6]1=[CH:7]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 11740710Pentacyclo[19.3.1.1~3,7~.1~9,13~.1~15,19~]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaeneYield 66%

Procedure

Calix (4) arene XXVI is prepared from 4-tert -butylcalix(4)arene (XXV; FIG. 13) as described (Gutsche, Levine, and Sujeeth, 1985). A hot solution of 5.0 g (6.75 mmol) of XXV in 250 ml of toluene is placed in a 500 ml three-necked round-bottom flask fitted with a mechanical stirrer and a gas inlet tube. The solution is cooled to 50°-55° C., treated with 5.0 g (37 mmol) of anhydrous AlCl3, and stirred for 2 h at 50°-55° C. in an inert atmosphere. The mixture is cooled in an ice bath and stirred with 125 ml of 1N HCl for 30 min, and the organic phase is separated and washed, dried, and evaporated to leave a yellow residue. This is triturated with 500 ml of ether, and the insoluble material is recrystallized from CHCl3 --CH3OH to yield 1.9 g (66%) of XXVI as off-white microcrystals. m.p. 313°-318° C.

Workup

  1. customfitted with a mechanical stirrer and a gas inlet tube
  2. temperatureThe solution is cooled to 50°-55° C.
  3. temperatureThe mixture is cooled in an ice bath
  4. customthe organic phase is separated
  5. washwashed
  6. customdried
  7. customevaporated
  8. customto leave a yellow residue
  9. customThis is triturated with 500 ml of ether
  10. customthe insoluble material is recrystallized from CHCl3

Sources & evidence

ORD record
ord-010bed3bea384286a539b57ecb49837f
Source dataset
uspto-grants-1995_08
Patent number
US05441983

Reaction notes

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