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

HRID 2351050Notes

Reaction equation

HRID 2351050 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 mmoles) and bis(triphenylphosphine) palladium chloride (0.20 mmoles) 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% Et2O/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% Et2O/hexane)

Sources & evidence

ORD record
ord-663f8541d6a74ea7a210face0114b828
Source dataset
uspto-grants-1989_10
Patent number
US04871771

Reaction notes

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