Hydrochloric Acid → 2-[1-(2-Benzyloxyethyl)cyclohexyl]ethanol

HRID 2223858Notes

Reaction equation

HRID 2223858 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][C:6]1([CH2:12][CH2:13][OH:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>CN(C)C=O.O>[CH2:15]([O:3][CH2:4][CH2:5][C:6]1([CH2:12][CH2:13][OH:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 76657Cyclohexane-1,1-diethanol

Product 1

HCID 597149852-[1-(2-Benzyloxyethyl)cyclohexyl]ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 60% sodium hydride/mineral oil (881 mg) in N,N-dimethylformamide (20 mL) was added 2-[1-(2-hydroxyethyl)cyclohexyl]ethanol (2.92 g) under ice cooling. To the solution was further added benzyl bromide (2.83 mL) under ice cooling, and it was stirred at room temperature for 63 hours. Water and 3N hydrochloric acid were added to the solution, and it was extracted with ethyl acetate. The organic layer was washed in turn with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=6:4) to give the title compound (2.93 g).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed in turn with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=6:4)

Sources & evidence

ORD record
ord-640c1ea70f184dc6981ffd1c36e76cae
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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