Ammonia → 2-Ethynylnaphthalene

HRID 436676

Reaction equation

HRID 436676 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].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

6

Reactant 4

HCID 222AmmoniaHCID 132302-VinylnaphthaleneHCID 24408Bromine2×HCID 24533Sodium amide

Product 1

HCID 1150172-Ethynylnaphthalene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 15.5 g. of 2-vinylnaphthalene and 300 ml. of chloroform, a 5 percent bromine in 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, acidified with dilute hydrochloric acid, and 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-468a3d89d2554877aa82ccae515f5a6d
Source dataset
uspto-grants-1977_02
Patent number
US04009197

Linked notes

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