Potassium tert-butoxide → HCID 13799283, compound

HRID 652315Notes

Reaction equation

HRID 652315 reaction equation
C([O-])(C)(C)C.[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[CH:17]=[C:18](Cl)[C:19]([F:22])([F:21])[F:20]>C(O)(C)(C)C>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[C:17]#[C:18][C:19]([F:20])([F:22])[F:21]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 54224598HCID 54224598, compound

Product 1

HCID 13799283HCID 13799283, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

30.7 g of potassium tertiary butanolate in 900 ml of tertiary butanol are introduced into a 1.5 l sulfonating flask with a thermometer, condenser, bubble counter and dropping funnel. 63.7 g (0.25 mole) of 1,3-dimethoxy-2-(2-chloro-3,3,3-trifluoroprop-1-enyl)-benzene in 100 ml of tertiary butanol are added dropwise to this clear, colourless solution (weakly exothermic) and the reaction is brought to completion by stirring at room temperature for 24 hours. The orange suspension is poured onto ice and extracted with ether and the extract is washed with water, N bicarbonate solution and brine, dried over magnesium sulfate and concentrated until crystals precipitate. The crystal mass is cooled, filtered cold and washed with a little ice-cold petroleum ether. 1,3-Dimethoxy-2-(3,3,3-trifluoroprop-1-ynyl)-benzene is obtained in the form of pale beige, fine crystals of melting point 110°-111° (yield 73%).

Workup

  1. custombubble counter
  2. additionThe orange suspension is poured onto ice
  3. extractionextracted with ether
  4. washthe extract is washed with water, N bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated until crystals
  7. customprecipitate
  8. temperatureThe crystal mass is cooled
  9. filtrationfiltered cold
  10. washwashed with a little ice-cold petroleum ether

Sources & evidence

ORD record
ord-8a0039f7cde847a3ad3196f3817a59d8
Source dataset
uspto-grants-1987_06
Patent number
US04670604

Reaction notes

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