Cyclohexane → HCID 59594958, compound

HRID 453563Notes

Reaction equation

HRID 453563 reaction equation
[CH3:1][CH:2]([OH:7])[CH2:3][CH2:4][CH2:5][Br:6].ClC(Cl)(Cl)C(=N)O[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1CCCCC1.FC(F)(F)S(O)(=O)=O>ClCCl>[Br:6][CH2:5][CH2:4][CH2:3][CH:2]([CH3:1])[O:7][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 8078CyclohexaneHCID 62406Trifluoromethanesulfonic acidHCID 144968Benzyl 2,2,2-trichloroacetimidateHCID 1104109062957-46-4

Product 1

HCID 59594958HCID 59594958, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-methyl-4-bromo-1-butanol (9.0 g, 0.05384 mol) and benzyl 2,2,2-trichloroacetimidate (16.3 g,) in a mixture of anhydrous cyclohexane (100 ml) and anhydrous dichloromethane (50 ml) cooled to 0° C., trifluoromethanesulfonic acid (1.0 ml) was added, and the mixture was stirred overnight at room temperature under argon. The mixture was filtered, washed with a saturated solution of NaHCO3 (250 ml) and deionized water (250 ml), and dried with anhydrous Na2SO4. The solvents were removed by distillation under reduced pressure. The crude product (9.2 g) was subjected to vacuum distillation, giving 7.2 g of colorless viscous liquid.

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with a saturated solution of NaHCO3 (250 ml) and deionized water (250 ml)
  3. dry with materialdried with anhydrous Na2SO4
  4. customThe solvents were removed by distillation under reduced pressure
  5. distillationThe crude product (9.2 g) was subjected to vacuum distillation

Sources & evidence

ORD record
ord-ef519b9184644717b34fc46ef329cb77
Source dataset
uspto-grants-2013_07
Patent number
US08492488B2

Reaction notes

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