Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Benzene, 1-(chloromethyl)-2-fluoro- | HCID 9580 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | (1R,2S)-2-methoxycyclohexanol | HCID 6951180 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 54099954 | HCID 54099954 | 88% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04282388 |
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| Source dataset | uspto-grants-1981_08 |
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| ORD ID | ord-9d8e949cac07436c8befbd2faccf123f |
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| Source note | uspto-grants-1981_08 |
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