Hydrochloric Acid → HCID 22375175, compound

HRID 1956091Notes

Reaction equation

HRID 1956091 reaction equation
[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].[H-].[Na+].Br[CH2:22][C:23]1([CH2:29][CH3:30])OCCC[O:24]1.BrCC(=O)CC.Cl>C1COCC1.C1(C)C=CC=CC=1.CN(C=O)C>[CH2:1]([CH:6]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][CH:15]([O:18][CH2:22][C:23](=[O:24])[CH2:29][CH3:30])[CH2:14][CH2:13]2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 131561-Bromo-2-butanoneHCID 24758Sodium hydrideHCID 3126233TRANS-4-(TRANS-4-PENTYLCYCLOHEXYL)CYCLOHEXANOLHCID 22375208HCID 22375208, compound

Product 1

HCID 22375175HCID 22375175, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 25.2 g (0.1 mol) of 4-(4-pentylcyclohexyl) cyclohexanol in 50 ml of THF was added dropwise to a mixture of 5.2 g (0.11 mol) of sodium hydride and 20 ml of THF at a temperature of lower than 10° C. Then, 50 ml of DMF was further added and stirred for 1 hour at a room temperature. While keeping inside of the reaction system at a temperature of lower than 0°C., a solution of 21 g (0.1 mol) of 2-bromomethyl-2-ethyl-1,3-dioxane derived from commercially available 1-bromo-2-butanone in 50 ml of THF was added dropwise, and stirred for 2 hours at a room temperature and then for 2 hours at 50° C. This solution was added with 50 ml of 6N hydrochloric acid, stirred for 1 hour at 50° C., added with 200 ml of toluene, and extracted. The organic layer was washed once with an aqueous solution saturated with potassium carbonate and twice with water, and dried over anhydrous magnesium sulfate. After the anhydrous magnesium sulfate was separated, the solvent was distilled off under a reduced pressure, and the residue thus obtained was subjected to a silica gel column chromatography (eluate: toluene) to obtain 20.9 g (yield 65%) of 4-(4-pentylcyclohexyl)-(2-oxobutyloxy)cyclohexane.

Workup

  1. customlower than 0°C.
  2. additionwas added dropwise
  3. stirringstirred for 2 hours at a room temperature
  4. waitfor 2 hours at 50° C
  5. stirringstirred for 1 hour at 50° C.
  6. extractionextracted
  7. washThe organic layer was washed once with an aqueous solution saturated with potassium carbonate and twice with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter the anhydrous magnesium sulfate was separated
  10. distillationthe solvent was distilled off under a reduced pressure
  11. customthe residue thus obtained

Sources & evidence

ORD record
ord-ec550bf550a44a51be783b946cc4f55d
Source dataset
uspto-grants-1998_07
Patent number
US05779936

Reaction notes

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