Sodium Chloride → 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzamide

HRID 893747Notes

Reaction equation

HRID 893747 reaction equation
[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[OH-:25].[K+].[Cl-].[Na+]>C(O)(C)(C)C>[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]#[C:15][C:16]3[CH:23]=[CH:22][C:19]([C:20]([NH2:21])=[O:25])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 136048264-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzonitrile

Product 1

HCID 197869944-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzamideYield 83%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 2.5 g (8 millimoles) of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-benzonitrile (Example 1), 60 ml of tert.-butanol and 7.5 g of potassium hydroxide powder was refluxed for 4 hours. The mixture was cooled, poured onto saturated sodium chloride solution and extracted twice with ether. The ether phases were washed with sodium chloride solution, dried over Na2SO4 and evaporated down to give 2.2 g (83%) of the pure title compound of melting point 220°-223° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted twice with ether
  4. washThe ether phases were washed with sodium chloride solution
  5. dry with materialdried over Na2SO4
  6. customevaporated down

Sources & evidence

ORD record
ord-b4e4fada0ef54ed3b1e23a775bc458a7
Source dataset
uspto-grants-1992_06
Patent number
US05126371

Reaction notes

Loading…