Cyclohexanemethanol → HCID 21897079, compound

HRID 1375439Notes

Reaction equation

HRID 1375439 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-aa5dc083e40c402fb6c4fcf5c3e8e947
Source dataset
uspto-grants-2007_01
Patent number
US07169784B2

Reaction notes

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