1-Butanol → Agn-190205

HRID 982047Notes

Reaction equation

HRID 982047 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 times 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/ H2O+0.1% of acetic acid; 100 ml/min; tR : 7 min).

Workup

  1. customThe cooled reaction mixture
  2. extractionthe solution was extracted three times 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-8b19f71395fc41f2b73a53ab5a32b5f3
Source dataset
uspto-grants-1991_02
Patent number
US04994489

Reaction notes

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