Water → 1-(4-Methylphenyl)-3-buten-1-ol

HRID 1612628Notes

Reaction equation

HRID 1612628 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[CH2:10](I)[CH:11]=[CH2:12].O>CN1C(=O)N(C)CC1>[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([CH:7]([OH:8])[CH2:12][CH:11]=[CH2:10])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 77254-MethylbenzaldehydeHCID 11166Allyl iodide

Product 1

HCID 42009971-(4-Methylphenyl)-3-buten-1-olYield 93%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Procedure

5.90 ml (50 mmol) p-tolualdehyde was dissolved in 150 ml of DMI, and 5.5 ml (60 mmol, 1.2 eq.) allyl iodide and 10.34 g (66 mmol, 1.3 eq.) SnF2 were added. The reaction became warm to the touch and much precipitate formed as the reaction progressed. After stirring for 1 hour at room temperature, 200 ml of H2O was added, the mixture was extracted with Et2O (1×250 ml, 2 ×100 ml), the combined Et2O layers were washed with sat. NH4Cl (3×50 ml, to remove excess DMI), dried over MgSO4, and evaporated in vacuo to an oil. Flash chromatography (1:4 EtOAc:hexanes, Rf 0.56) yielded 7.5 g (93%) of product as a clear oil. 1H NMR (CDCl3): 7.25 and 7.15 (4H, phenyl), 5.8 and 5.15 (3H, vinyl), 4.65 (1H, CHOH), 2.5 (2H, CH2), 2.35 (2H, CH2), 2.35 (3H, CH3), and 2.15 (1H, OH) ppm.

Workup

  1. temperatureThe reaction became warm to the touch and much precipitate
  2. customformed as the reaction
  3. extractionthe mixture was extracted with Et2O (1×250 ml, 2 ×100 ml)
  4. washthe combined Et2O layers were washed with sat. NH4Cl (3×50 ml, to remove excess DMI)
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo to an oil

Sources & evidence

ORD record
ord-fcd3d16084f94773b4f0315a255816c1
Source dataset
uspto-grants-1993_03
Patent number
US05190929

Reaction notes

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