Hydroquinone → Chloroadamantylidene adamantane

HRID 247152

반응식

HRID 247152 반응식
[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

참가 물질

5

반응물 3

HCID 785HydroquinoneHCID 31398ChlorosuccinimideHCID 141567Biadamantylidene

생성물 1

HCID 12950367Chloroadamantylidene adamantane

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-32e7d03f339d472298f70a06cd4b7f25
출처 데이터셋
uspto-grants-1987_11
특허 번호
US04705847

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