Cyclohexanemethanol → HCID 21897079, compound

HRID 2056653Notes

Reaction equation

HRID 2056653 reaction equation
[N:1]1[C:8](Cl)=[N:7][C:5]([Cl:6])=[N:4][C:2]=1[Cl:3].C(=O)(O)[O-].[K+].[CH:15]1([CH2:21][OH:22])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>C1(C)C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1>[Cl:3][C:2]1[N:4]=[C:5]([Cl:6])[N:7]=[C:8]([O:22][CH2:21][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[N:1]=1

Participants

6

Reactant 3

HCID 7507CyclohexanemethanolHCID 7954Cyanuric chlorideHCID 516893Potassium Bicarbonate

Product 1

HCID 21897079HCID 21897079, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 1140TolueneSolvent2×

Procedure

To cyanuric chloride (3.76 g, 20.0 mmol) dissolved in toluene (20 mL) was added potassium bicarbonate (2.80 g, 20.0 mmol) and 18-crown-6 (0.1614 g, 0.6 mmol) followed by dropwise addition of cyclohexylmethanol (2.5 mL, 20 mmol) in 15 mL of toluene (15 mL). The reaction mixture was allowed to stir at reflux for about 18 hours under nitrogen. The reaction mixture was passed through a plug of Celite and concentrated using a rotary evaporator and dried over night under vacuum to give 113 as an oil (5.212 g, 99% recovery).

Workup

  1. temperatureat reflux for about 18 hours under nitrogen
  2. concentrationconcentrated
  3. customa rotary evaporator
  4. customdried over night under vacuum

Sources & evidence

ORD record
ord-e85cc8f4f6c94973b3b14b09d2d74562
Source dataset
uspto-grants-2008_02
Patent number
US07335656B2

Reaction notes

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