Ethanol → HCID 23039690, compound

HRID 2166405Notes

Reaction equation

HRID 2166405 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][CH2:13][CH3:14])[O:11][CH2:10]1.B(F)(F)F.C[CH2:20][O:21]CC.[CH2:24](O)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][CH3:24])([CH2:12][CH2:13][CH3:14])[CH2:20][OH:21]

Participants

4

Reactant 3

HCID 702Ethanol2×HCID 8000Boron trifluoride etherateHCID 230396712-(2,4-Dichlorophenyl)-2-propyloxirane

Product 1

HCID 23039690HCID 23039690, compound

Procedure

27.6 g (120 mmoles) of 2-(2,4-dichlorophenyl)-1,2-epoxypentane are dissolved in 60 ml of ethanol. A solution of 17.4 g (120 mmoles) of boron trifluoride-etherate in 60 ml of ethanol is added dropwise at 0° C., the internal temperature being kept at 0°-5° C. by cooling with ice water. The mixture is then left at +7° C. to react further slowly. As soon as epoxide can no longer be detected by gas chromatography, the reaction mixture is extracted with methylene chloride. The combined extracts are washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The yield of crude product is 32.3 g. Purification by column chromatography (silica gel; 4:1 petroleum ether/ethyl acetate) gives 15.96 g (53% of theory, taking into account that the epoxide employed is 90% pure). Boiling point 90° C./0.07mbar. 100 MHz-1H-NMR (CDCl3): δ=7.0-7.6 ppm (m, aromatic H); 3.7-4.4 ppm (m, --CH2OH); 3.2-36 ppm (q, --OCH2CH3); 1.6-2.2 ppm (m, --CH2 --, OH); 0.7-1.4 ppm (t, --OCH2CH3 and ##STR21##

Workup

  1. custombeing kept at 0°-5° C.
  2. waitThe mixture is then left at +7° C.
  3. customto react further slowly
  4. extractionthe reaction mixture is extracted with methylene chloride
  5. washThe combined extracts are washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by column chromatography (silica gel; 4:1 petroleum ether/ethyl acetate)
  10. customgives 15.96 g (53% of theory

Sources & evidence

ORD record
ord-c65a4eb66400495c8ec3f51689f3c8e8
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

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