Ammonia → 2-Ethynylnaphthalene

HRID 2071850Notes

Reaction equation

HRID 2071850 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-4f51a6fbfbe0487db82fd9356ff5128a
Source dataset
uspto-grants-1977_09
Patent number
US04048330

Reaction notes

Loading…