2-Chloroethanol → (2-Decyloxy)ethanol

HRID 2287282Notes

Reaction equation

HRID 2287282 reaction equation
[OH-].[K+].O1CCCCC1OC1CCCCO1.Cl[CH2:17][CH2:18][OH:19].[CH2:20]([OH:30])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:18]([OH:19])[CH2:17][O:30][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

7

Reactant 4

HCID 342-ChloroethanolHCID 81741-DecanolHCID 14797Potassium HydroxideHCID 263182Tetrahydropyranyl ether

Product 1

HCID 62806(2-Decyloxy)ethanol

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 1140TolueneSolvent

Procedure

44.88 g (800 mmol) of fine powdered potassium hydroxide is added to 32.93 g (200 mmol) of the tetrahydropyranyl ether of 2-chloroethanol, 1 g (3.6 mmol) of tetrabutylammonium chloride and 20 g (126.36 mmol) of decan-1-ol in 300 ml of toluene, and it is refluxed for 24 hours. Solid is filtered out, and the filtrate is evaporated to the dry state. 500 ml of ethanol/50 ml of 10% aqueous hydrochloric acid are added to the residue (oil) that is thus obtained, and it is stirred for one hour at room temperature. It is evaporated to the dry state in a vacuum, and the residue is chromatographed on silica gel (mobile solvent: hexane/acetone=20:1).

Workup

  1. temperatureis refluxed for 24 hours
  2. filtrationSolid is filtered out
  3. customthe filtrate is evaporated to the dry state
  4. addition500 ml of ethanol/50 ml of 10% aqueous hydrochloric acid are added to the residue (oil) that
  5. customis thus obtained
  6. customIt is evaporated to the dry state in a vacuum
  7. customthe residue is chromatographed on silica gel (mobile solvent: hexane/acetone=20:1)

Sources & evidence

ORD record
ord-c34d379adb42474184393a8733a1c208
Source dataset
uspto-grants-2000_07
Patent number
US06083479

Reaction notes

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