2-Methyl-3-butyn-2-ol → 4-(4-Butylphenyl)-2-methyl-3-butyn-2-ol

HRID 1707895Notes

Reaction equation

HRID 1707895 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[CH3:12][C:13]([OH:17])([CH3:16])[C:14]#[CH:15]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:12][C:13]([OH:17])([CH3:16])[C:14]#[C:15][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 5210591-Bromo-4-butylbenzene

Product 1

HCID 189599944-(4-Butylphenyl)-2-methyl-3-butyn-2-olYield 41.9%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

1-Bromo-4-butylbenzene (235 g), 3-methyl-1-butyne-3-ol (139 g), triphenylphosphine (4.8 g) and bis(triphenylphosphine)palladium(II) chloride (2.8 g) were dissolved in triethylamine (1,000 ml), and then copper(I) iodide (0.8 g) was added thereto. After stirring at room temperature for 1 hour, the reaction mixture was further stirred at 90° C. for 5 hours. The resulting precipitated crystals were filtered, and then triethylamine was distilled off therefrom, followed by extracting with chloroform. The resultant was washed with 10% hydrochloric acid twice, and further with water twice, and then chloroform was distilled off therefrom. The residue was purified using silica gel-chloroform column chromatography to give 3-methyl-1-(4'-butylphenyl)-1-butyne-3-ol (100 g).

Workup

  1. stirringthe reaction mixture was further stirred at 90° C. for 5 hours
  2. customThe resulting precipitated crystals
  3. filtrationwere filtered
  4. distillationtriethylamine was distilled off
  5. extractionby extracting with chloroform
  6. washThe resultant was washed with 10% hydrochloric acid twice
  7. distillationfurther with water twice, and then chloroform was distilled off
  8. customThe residue was purified

Sources & evidence

ORD record
ord-f4b09eafe8e443e4a4295089bb11db65
Source dataset
uspto-grants-1994_10
Patent number
US05356558

Reaction notes

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