Boron trifluoride etherate → HCID 23039737, compound

HRID 2166404Notes

Reaction equation

HRID 2166404 reaction equation
B(F)(F)F.C[CH2:6][O:7]CC.[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[C:18]1([CH2:21][CH2:22][CH3:23])[O:20][CH2:19]1.C(=O)(O)[O-].[Na+]>CO>[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[C:18]([O:20][CH3:19])([CH2:21][CH2:22][CH3:23])[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 230396712-(2,4-Dichlorophenyl)-2-propyloxirane

Product 1

HCID 23039737HCID 23039737, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

12.5 ml of boron trifluoride ethyl etherate are added dropwise slowly to a solution of 20.7 g (90 mmoles) of 2-(2,4-dichlorophenyl)-1,2-epoxypentane in 100 ml of absolute methanol. The temperature is kept at 18°-20° C. by occasional cooling. The temperature is then kept at 18°-20° C. for a further 6 hours, and the mixture is then stirred for a further hour at 30° C. The solution is poured into ice-cold, dilute sodium bicarbonate solution, and the resulting mixture is extracted twice with diethyl ether. The combined ether extracts are washed twice with half-saturated sodium bicarbonate solution and then twice with sodium chloride solution and are dried over sodium sulfate, filtered and concentrated. This gives 26.2 g of a yellowish, slightly viscous liquid, which is distilled in a high vacuum using a Vigreux column. The 2-(2,4-dichlorophenyl)-2-methoxypentan-1-ol thus obtained is a colourless, viscous oil of boiling point 88°-90° C./10.7×10-3 mbar and n50D 1.5322. Yield 12.1 g (=51% of theory), 100 mHz-1H-NMR(CDCl3): δ=7.15-7.6 ppm (m, 3H, aromatic); 4.1 ppm (dd, 2H, --CH2OH); 3.25 ppm (s, 3H, --OCH3); 1.7-2.3 ppm (m, 3H, ##STR19## 1H disappears on adding D2O); 0.7-1.25 ppm (m, 5H, --CH2CH2CH3).

Workup

  1. customis kept at 18°-20° C. by occasional cooling
  2. extractionthe resulting mixture is extracted twice with diethyl ether
  3. washThe combined ether extracts are washed twice with half-saturated sodium bicarbonate solution
  4. dry with materialtwice with sodium chloride solution and are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationThis gives 26.2 g of a yellowish, slightly viscous liquid, which is distilled in a high vacuum

Sources & evidence

ORD record
ord-bf73aee9dc54441fba254a5ce97e106e
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

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