Hydroquinone → Chloroadamantylidene adamantane

HRID 247152

Reaktionsgleichung

Reaktionsgleichung von HRID 247152
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[C:11]1[CH:18]3[CH2:19][CH:14]4[CH2:15][CH:16]([CH2:20][CH:12]1[CH2:13]4)[CH2:17]3)[CH2:8]2.[Cl:21]N1C(=O)CCC1=O.C1(C=CC(O)=CC=1)O>C(Cl)Cl>[Cl:21][C:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[C:2]1=[C:11]1[CH:12]3[CH2:20][CH:16]4[CH2:15][CH:14]([CH2:19][CH:18]1[CH2:17]4)[CH2:13]3)[CH2:10]2

Komponenten

5

Edukt 3

HCID 785HydroquinoneHCID 31398ChlorosuccinimideHCID 141567Biadamantylidene

Produkt 1

HCID 12950367Chloroadamantylidene adamantane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1 mmol (268 mg) adamantylidene adamantane having the formula 19 in 20 cm3CH2Cl2, 1.05 mmoles (140 mg) N-chlorosuccinimide was added. The reaction mixture was stirred at room temperature for 1 hour, diluted with CH2Cl2, and washed twice with water. The organic layer was dried with MgSO4 and evaporated. The yield of 4-eq.-chloroadamantylideneadamantane was 300 mg (98%), melting point: 142°-143° C. (literature: 144°-145° C.). 1H NMR (CDCl3): δ 4.15 (br s, 1H); 3.05 (br s 1H); 2.8 (br s, 3H); 2.6-1.15 (br m, 22H) ppm. When 0.1 mmol hydroquinone was added to the solution, exactly the same reaction occurred, and the product could be isolated in virtually the same quantitative yield.

Aufarbeitung

  1. washwashed twice with water
  2. dry with materialThe organic layer was dried with MgSO4
  3. customevaporated
  4. custom300 mg (98%), melting point: 142°-143° C. (literature: 144°-145° C.)
  5. customexactly the same reaction
  6. customthe product could be isolated in virtually the same quantitative yield

Quellen und Nachweise

ORD-Eintrag
ord-32e7d03f339d472298f70a06cd4b7f25
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705847

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