tert-Butanol → HCID 14597331, compound

HRID 1742724Notes

Reaction equation

HRID 1742724 reaction equation
CC([O-])(C)C.[K+].CC(O)(C)C.[CH2:12]([O:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)[C:13]#[CH:14]>O>[CH:12]([O:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)=[C:13]=[CH2:14]

Participants

5

Reactant 3

HCID 6386tert-Butanol2×HCID 29132Naphthalene, 1-(2-propynyloxy)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 14597331HCID 14597331, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a similar reaction vessel as used in the abovementioned reaction, were placed 1.532 parts of t-BuOK and 6.816 parts of t-BuOH and to this, a mixture of 10.000 parts of 1-propargyloxynaphthalene and 23.333 parts of t-BuOH was dropwise added. The content was reacted at 50° C. for 60 minutes and then deionized water was added to stop the reaction. t-BuOH layer and water layer were removed off by using an evaporator, and the residue was added with an aqueous NaOH solution, extracted with an ether and the ether layer was separated. The ether solvent was removed off and the residue was subjected to a column chromatography (silica gel 200 mesh) to obtain a purified 1-allenyloxy naphthalene as a colorless oily product.

Workup

  1. customInto a similar reaction vessel as used in the abovementioned reaction
  2. additionwas dropwise added
  3. customThe content was reacted at 50° C. for 60 minutes
  4. additionwas added
  5. customthe reaction
  6. customt-BuOH layer and water layer were removed off
  7. customan evaporator
  8. additionthe residue was added with an aqueous NaOH solution
  9. extractionextracted with an ether
  10. customthe ether layer was separated
  11. customThe ether solvent was removed off

Sources & evidence

ORD record
ord-599d5f305f2d4677b91a38cba111bb29
Source dataset
uspto-grants-1994_08
Patent number
US05340931

Reaction notes

Loading…