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

HRID 1382433Notes

Reaction equation

HRID 1382433 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-259a9af4d9784a89b0a1169be5caaad7
Source dataset
uspto-grants-1989_02
Patent number
US04806558

Reaction notes

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