Diiodomethane → 2-Cyclopropylnaphthalene

HRID 1284336Notes

Reaction equation

HRID 1284336 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1)=[CH2:2].I[CH2:14]I>[Cu].[Zn].C(OCC)C>[CH:1]1([C:3]2[CH:12]=[CH:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=2)[CH2:14][CH2:2]1

Participants

5

Reactant 2

HCID 6346DiiodomethaneHCID 132302-Vinylnaphthalene

Product 1

HCID 146686962-Cyclopropylnaphthalene

Reagents, catalysts & solvents 2

HCID 10290809Zinc copper coupleCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 15.5 g. of 2-vinylnaphthalene, 23 g. of diiodomethane, 19.6 g. of zinc-copper couple (comprising 19.5 g. of zine and 0.1 g. of copper) and 500 ml. of diethyl ether is refluxed for eight hours; the cooled mixture is then filtered, washed with dilute hydrochloric acid, washed with water to neutrality, dried and evaporated to yield 2-cyclopropylnaphthalene.

Workup

  1. additionA mixture of 15.5 g
  2. filtrationthe cooled mixture is then filtered
  3. washwashed with dilute hydrochloric acid
  4. washwashed with water to neutrality
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-9631842422ce4c9d95e92d9050a05e90
Source dataset
uspto-grants-1976_08
Patent number
US03978116

Reaction notes

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