Water → (S)-2-fluorooctane-1-ol

HRID 1088589Notes

Reaction equation

HRID 1088589 reaction equation
N1C=CC=CC=1.[FH:7].[O:8]1[C@H:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9]1.O.CCCCCCC>CCOCC>[F:7][C@@H:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8900HeptaneHCID 64774Pyridine, hydrofluoride (1:1)HCID 1620686(2R)-2-Hexyloxirane

Product 1

HCID 11137325(S)-2-fluorooctane-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 30 ml of hydrogen fluoride pyridine solution which was cooled with ice, 8.5 g of (R)-1,2-epoxyoctane in 20 ml of ether was added dropwise. The mixture was stirred for one hour at the same temperature and brought to room temperature. 100 ml of water was added to the mixture. After extracting it with 50 ml of ether twice, the obtained organic layer was washed with an alkali solution and then with water, dried over magnesium sulfate and concentrated. The concentrate was distilled under reduced pressure and 4.9 g of distillate was obtained at 126°-129° C./80 mmHg. 3.7 g of (S)-2-fluorooctane-1-ol was obtained by recrystallization from 40 ml of heptane. Its melting point was 33°-35° C., [α]D26 -13.14 (c1.7, benzene) of optical rotation was shown.

Workup

  1. additionwas added dropwise
  2. custombrought to room temperature
  3. extractionAfter extracting it with 50 ml of ether twice
  4. washthe obtained organic layer was washed with an alkali solution
  5. dry with materialwith water, dried over magnesium sulfate
  6. concentrationconcentrated
  7. distillationThe concentrate was distilled under reduced pressure and 4.9 g of distillate
  8. customwas obtained at 126°-129° C./80 mmHg

Sources & evidence

ORD record
ord-198aa2c8b4d8469c9d0ab25f99a4fe90
Source dataset
uspto-grants-1990_10
Patent number
US04963288

Reaction notes

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