1-Propanol → HCID 23039677, compound

HRID 2166410Notes

Reaction equation

HRID 2166410 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.[CH2:14]([OH:17])CC.B(F)(F)F.[CH3:22][CH2:23]OCC>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]([O:11][CH2:10][CH2:22][CH3:23])([CH2:12][CH3:13])[CH2:14][OH:17]

Participants

4

Reactant 3

HCID 10311-Propanol2×HCID 8000Boron trifluoride etherateHCID 23039726HCID 23039726, compound

Product 1

HCID 23039677HCID 23039677, compound

Procedure

8.68 g (0.04 mole) of 2-(2,4-dichlorophenyl)-1,2-epoxybutane of 95% purity are dissolved in 12 g (0.2 mole) of n-propanol, and a solution of 5.68 g (0.04 mole) of boron trifluoride-etherate in 12 g (0.2 mole) of n-propanol is added dropwise at 20° C. After 24 hours, the mixture is extracted with chloroform, the solvent is removed on a rotary evaporator and the residue is purified by column chromatography using silica gel. The yield is 5.41 g (48.8%) of a colourless oil. 60 MHz-1H-NMR (DCCl3): δ=7.0-7.6 ppm (m, 3H, aromatic); 3.7-4.4 ppm (m, 2H, CH2OH); 3.3 ppm (t, 2H, OCH2CH2 --); 1.4-2.6 (m, 5H, 2×CH2, OH); 0.5-1.3 ppm (m, 6H, 2×CH3).

Workup

  1. extractionthe mixture is extracted with chloroform
  2. customthe solvent is removed on a rotary evaporator
  3. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-46f9b4c59e8d4bb6a25f7ec9b75ebbc2
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

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