1-Butanol → Agn-190205

HRID 1657134Notes

Reaction equation

HRID 1657134 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]3C=CC(C#N)=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[OH-:25].[K+].[CH2:27]([OH:31])[CH2:28][CH2:29][CH3:30]>O>[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:17]=[CH:18][C:28]([C:27]([OH:25])=[O:31])=[CH:29][CH:30]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 2631-ButanolHCID 14797Potassium HydroxideHCID 136048264-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)ethynyl]-benzonitrile

Product 1

HCID 10314719Agn-190205Yield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.6 g (8 millimoles) of 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphth-2-yl)-ethynyl]-benzonitrile (Example 1) and 4.6 g of 85% strength potassium hydroxide in 17 ml of n-butanol were refluxed for 1.5 hours. The cooled reaction mixture was dissolved in 100 ml of water and the solution was extracted three time$ with ether. The aqueous phase was freed from residual ether under reduced pressure and acidified with 2N HCl. The precipitate which had separated out was filtered off under suction, washed with water and dried in a stream of nitrogen. 2.1 g of crude product remained. Recrystallization from isopropanol gave 1.2 g (44%) of the title compound of melting point 252°-256° C., which had a purity of 99.9% according to HPLC (C18 reversed phase; 9:1 acetonitrile/H2 +0.1% of acetic acid; 100 ml/min; tR : 7 min).

Workup

  1. customThe cooled reaction mixture
  2. extractionthe solution was extracted three time$ with ether
  3. customThe precipitate which had separated out
  4. filtrationwas filtered off under suction
  5. washwashed with water
  6. customdried in a stream of nitrogen
  7. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-2570d53d36c84fb28555076a9489ee10
Source dataset
uspto-grants-1993_10
Patent number
US05256694

Reaction notes

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