Water → HCID 54099954, compound

HRID 894153Notes

Reaction equation

HRID 894153 reaction equation
[OH-].[Na+].[CH3:3][O:4][C@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]1[OH:11].[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Cl.O>CS(C)=O>[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][O:11][C@@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10][C@@H:5]1[O:4][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 14798Sodium HydroxideHCID 6951180(1R,2S)-2-methoxycyclohexanol

Product 1

HCID 54099954HCID 54099954, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
45 °C

Procedure

772 g (19.3 mol) of sodium hydroxide powder were added in portions to 1,672 g (12.8 mol) of cis-2-methoxycyclohexanol and 1,853 g (12.8 mol) of 2-fluorobenzyl chloride in 10 l of dimethylsulphoxide, whilst cooling with water. The mixture was stirred at 35° C. for 2 hours and at 45° C. overnight. Thereafter, it was cooled to 18° C., 10 l of petroleum ether were added and the mixture was discharged onto 10 ml of ice-water. The organic phase was separated off, extracted by shaking with water, dried over sodium sulphate and filtered and the filtrate was concentrated. The oily residue was distilled. 2,685 g (87.5% of theory) of cis-1-(2-fluorobenzyloxy)-2-methoxy-cyclohexane of boiling point 150° C./2 mm Hg were obtained.

Workup

  1. temperatureThereafter, it was cooled to 18° C.
  2. customThe organic phase was separated off
  3. extractionextracted
  4. stirringby shaking with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. distillationThe oily residue was distilled

Sources & evidence

ORD record
ord-9d8e949cac07436c8befbd2faccf123f
Source dataset
uspto-grants-1981_08
Patent number
US04282388

Reaction notes

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