1-Butanol → HCID 23039675, compound

HRID 2166407Notes

Reaction equation

HRID 2166407 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:11])[O:10][CH2:9]2)=[CH:4][CH:3]=1.C(O)[CH2:13][CH2:14][CH3:15].B(F)(F)F.C[CH2:22][O:23]CC>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH2:9][CH2:13][CH2:14][CH3:15])([CH3:11])[CH2:22][OH:23])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 2631-Butanol2×HCID 8000Boron trifluoride etherateHCID 178694862-(4-Fluorophenyl)-2-methyloxirane

Product 1

HCID 23039675HCID 23039675, compound

Procedure

A solution of 4.56 g (30 mmoles) of 2-(4-fluorophenyl)-1,2-epoxypropane in 5.55 g (75 mmoles) of n-butanol is added dropwise slowly at an internal temperature of 5°-7° C., with cooling, to a solution of 2.13 g (0.016 mole) of boron trifluoride ethyl etherate in 5.55 g (75 mmoles) of n-butanol, and the temperature is kept at +7° C. for a further 4 hours. The reaction mixture is then worked up by extraction (methylene chloride) and washing with water. The organic phase is dried over sodium sulfate, filtered and concentrated in vacuo. Distillation of the crude product gives 4.48 g (=66% of theory) of the pure end product in the form of a colourless oil. Boiling point 120°-125° C./20 mbar. 100 MHz-1H-NMR (CDCl3): δ=6.8-7.5 ppm (m, 4H aromatic); 3.5 ppm (q, 2H, --CH2OH); 3.2 ppm (m, 2H, --OCH2 --); 2.3 ppm (broad, 1H, --OH); 1.6 ppm (s, 3H, --CH3); 1.4 ppm (m, 4H, --CH2CH2 --); 0.9 ppm (t, 3H, --CH3).

Workup

  1. extractionThe reaction mixture is then worked up by extraction (methylene chloride)
  2. washwashing with water
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. distillationDistillation of the crude product
  7. customgives 4.48 g (=66% of theory) of the pure end product in the form of a colourless oil

Sources & evidence

ORD record
ord-54806e9a79ee4e5ab7372fda766f34d9
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

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