Hydrochloric Acid → 1-Ethynyl-4-methoxybenzene

HRID 857837Notes

Reaction equation

HRID 857837 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10](P(C12CC3CC(CC(C3)C1)C2)C12CC3CC(CC(C3)C1)C2)[CH2:11]CC.Cl>C1COCC1.[Cl-].[Zn+2].[Cl-].CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]#[CH:11])=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 121674-ChloroanisoleHCID 11371790Bis(adamantan-1-yl)(butyl)phosphane

Product 1

HCID 2510201-Ethynyl-4-methoxybenzeneYield 76%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3007855ZincchlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

50 mmol of anhydrous zinc chloride (dissolved in 40 ml of THF) were added at 0° C to a suspension of 50 mmol of ethynyllithium-ethylenediamine complex in 40 ml of THF. After heating to RT for half an hour, the solution was again cooled to 0° C. and 40 mmol of 4-chloroanisole, 0.05 mol % of Pd(OAc)2 and 0.1 mol % of butyldiadamantylphosphine were added. The reaction mixture was stirred at 25 to 50° C. until conversion was complete. 2 M HCl solution was then added to the reaction solution. After extraction with ether, washing of the ether phase and distillation, 76% of p-methoxyphenylacetylene is obtained.

Workup

  1. temperaturethe solution was again cooled to 0° C.
  2. extractionAfter extraction with ether
  3. washwashing of the ether phase and distillation

Sources & evidence

ORD record
ord-badf2b6339ee4901a86861d3d7402b3d
Source dataset
uspto-grants-2006_12
Patent number
US07148176B2

Reaction notes

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