1-Dodecyne → 2-(1-Dodecyn-1-yl)benzaldehyde

HRID 620537Notes

Reaction equation

HRID 620537 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>[C:10]([C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5])#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 2

HCID 698211-DodecyneHCID 811292-Bromobenzaldehyde

Product 1

HCID 197787892-(1-Dodecyn-1-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 2-bromobenzaldehyde (10.05 mmoles), 1-dodecyne (12.03 mmoles), cuprous iodide (0.11 mmole) and bis(triphenylphosphine) palladium chloride (0.20 mmole) in freshly distilled triethylamine (30 ml.) was heated for one hour at reflux producing a white precipitate. The reaction mixture was cooled and filtered. The filtrate was evaporated to dryness at reduced pressure and then dissolved in diethyl ether (50 ml) and washed with brine (50 ml). After treatment with anhydrous magnesium sulfate and charcoal, the solution was evaporated to afford a dark oil, which was purified by flash chromatography (2% diethyl ether/hexane) to yield the desired product.

Workup

  1. temperaturewas heated for one hour
  2. temperatureat reflux
  3. customproducing a white precipitate
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness at reduced pressure
  7. dissolutiondissolved in diethyl ether (50 ml)
  8. washwashed with brine (50 ml)
  9. customAfter treatment with anhydrous magnesium sulfate and charcoal, the solution was evaporated
  10. customto afford a dark oil, which
  11. customwas purified by flash chromatography (2% diethyl ether/hexane)

Sources & evidence

ORD record
ord-78106302930e4cba969dea469a09e02d
Source dataset
uspto-grants-1989_04
Patent number
US04820719

Reaction notes

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