Allyl Alcohol → HCID 23039696, compound

HRID 2166409Notes

Reaction equation

HRID 2166409 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:12][CH3:13])[O:11][CH2:10]1.B(F)(F)F.C[CH2:19][O:20]CC.[CH2:23](O)[CH:24]=C>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([O:11][CH2:10][CH:23]=[CH2:24])([CH2:12][CH3:13])[CH2:19][OH:20]

Participants

4

Reactant 3

HCID 7858Allyl AlcoholHCID 8000Boron trifluoride etherateHCID 23039726HCID 23039726, compound

Product 1

HCID 23039696HCID 23039696, compoundYield 108.1%

Procedure

8.68 g (38 mmoles) of 2-(2,4-dichlorophenyl)-1,2-epoxybutane of 95% purity are added dropwise at 7°-8° C. to a solution of 5.67 g (40 mmoles) of boron trifluoride-etherate in 23.2 g (400 mmoles) of allyl alcohol. The mixture is kept at 20° C. overnight in a water bath, and the solution is extracted with chloroform and water. Drying the organic phase with Na2SO4 and removing the solvent on a rotary evaporator gives 11.3 g of crude product, which is purified by column chromatography (silica gel; mobile phase: 4 parts of petroleum ether/1 part of ethyl acetate). The yield of pure product is 5.28 g (50.5% of theory) of a colourless oil. Refractive index n50D =1.5291. 60 MHz-1H-NMR(DCCl3): δ=7.1-7.6 ppm (m, 3H, aromatic); 5.0-6.5 ppm (m, 3H; olefinic): 3.8-4.4 ppm (m, 4H; 2× OCH2) 1.5-2.5 ppm (m; 3H CH2CH3, OH); 0.67 ppm (t, 3H, CH2CH3).

Workup

  1. extractionthe solution is extracted with chloroform and water
  2. dry with materialDrying the organic phase with Na2SO4
  3. customremoving the solvent
  4. customon a rotary evaporator

Sources & evidence

ORD record
ord-666aae166e624b67908da71dde1107be
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

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