Hydroquinone → Chloroadamantylidene adamantane

HRID 247152

Reaction equation

HRID 247152 reaction equation
[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

Participants

5

Reactant 3

HCID 785HydroquinoneHCID 31398ChlorosuccinimideHCID 141567Biadamantylidene

Product 1

HCID 12950367Chloroadamantylidene adamantane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-32e7d03f339d472298f70a06cd4b7f25
Source dataset
uspto-grants-1987_11
Patent number
US04705847

Linked notes

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