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 1654964ノート

反応式

HRID 1654964 の反応式
[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

参加物

4

反応物 3

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

生成物 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-dodecaene収率 66%

実験手順

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, 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.

後処理

  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

出典と根拠

ORDレコード
ord-0bb80e979ef3418da5359c852a2aaa6e
出典データセット
uspto-grants-1995_04
特許番号
US05409959

反応ノート

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