Ammonia → 2-Ethynylnaphthalene

HRID 840016

Reaction equation

HRID 840016 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].C(Cl)(Cl)Cl.[Br].BrBr.N.[NH2-].[Na+]>C(Cl)(Cl)Cl>[C: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)#[CH:2]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 132302-VinylnaphthaleneHCID 24408BromineHCID 24533Sodium amideHCID 178478473HCID 178478473, compound

Product 1

HCID 1150172-Ethynylnaphthalene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 15.5 g. of 2-vinylnaphthalene and 300 ml. of chloroform, a 5% bromine chloroform solution is added at -10° C until the bromine color persists. The mixture is then added to 200 ml. of ammonia containing 15 g. of sodium amide. The mixture is allowed to evaporate; the residue is extracted with diethyl ether. The extracts are combined, washed to neutrality with water, dried, and evaporated to yield 2-ethynylnaphthalene.

Workup

  1. additionTo a mixture of 15.5 g
  2. additionThe mixture is then added to 200 ml
  3. customto evaporate
  4. extractionthe residue is extracted with diethyl ether
  5. washwashed
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-57774d12659e40cbb6a9f98b4491b09a
Source dataset
uspto-grants-1978_06
Patent number
US04097674

Linked notes

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