tert-Butanol → 1-Ethynyl-4-propylbenzene

HRID 1440179Notes

Reaction equation

HRID 1440179 reaction equation
CC(C)([O-])C.[K+].C(O)(C)(C)C.[CH2:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21](Cl)=[CH2:22])=[CH:17][CH:16]=1)[CH2:13][CH3:14]>O>[CH2:12]([C:15]1[CH:16]=[CH:17][C:18]([C:21]#[CH:22])=[CH:19][CH:20]=1)[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 18982654HCID 18982654, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 27751331-Ethynyl-4-propylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Potassium t-butoxide (21.5 g) was added to stirred t-butanol and warmed to gentle reflux. The alkene product from step 2.3 (20 g) was added dropwise and then the mixture was heated under reflux for 3 hrs. Water (100 ml) was added and the product extracted into petroleum spirit (3×100 ml), washed with 10% HCl and water. The crude alkine product was 97% pure by gc. Yield 12 g.

Workup

  1. temperaturewarmed to gentle reflux
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 hrs
  4. extractionthe product extracted into petroleum spirit (3×100 ml)
  5. washwashed with 10% HCl and water

Sources & evidence

ORD record
ord-64cee7c580a741c39a8980fa15705e07
Source dataset
uspto-grants-1996_03
Patent number
US05498366

Reaction notes

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