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

HRID 982053Notes

Reaction equation

HRID 982053 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-8885fa5d265f404d8009ebd04868626c
Source dataset
uspto-grants-1991_02
Patent number
US04994489

Reaction notes

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