Hydrochloric Acid → HCID 54320888, compound

HRID 1280253Notes

Reaction equation

HRID 1280253 reaction equation
[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[OH-].[Na+].[C:10]([O:14][N:15]=[C:16]([CH2:18]Cl)[CH3:17])([CH3:13])([CH3:12])[CH3:11].Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCCC1>[C:10]([O:14][N:15]=[C:16]([CH2:18][O:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][OH:7])[CH3:17])([CH3:13])([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 81051,5-PentanediolHCID 14798Sodium HydroxideHCID 54209658HCID 54209658, compound

Product 1

HCID 54320888HCID 54320888, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

First, 13.02 g of 1,5-pentanediol, 2.40 g of sodium hydroxide (powdery), 1.14 g of benzyltriethylammonium chloride, and 100 ml of tetrahydrofuran were placed in a reaction vessel, to which 8.18 g of chloroacetone O-tert-butyloxime was slowly added dropwise with stirring under heating under reflux. After further stirring for 8 hours, the reaction mixture was poured into diluted hydrochloric acid, and extracted twice with ethyl acetate. The ethyl acetate layers were combined, washed with diluted hydrochloric acid and water in this order, dried over anhydrous magnesium sulfate, and concentrated to give a crude product. This crude product was subjected to silica gel chromatography, which afforded 6.79 g (yield, 59%) of 5-hydroxypentyloxyacetone O-tert-butyloxime, nD20.0 1.4493.

Workup

  1. additionwas slowly added dropwise
  2. temperatureunder heating
  3. temperatureunder reflux
  4. stirringAfter further stirring for 8 hours
  5. extractionextracted twice with ethyl acetate
  6. washwashed with diluted hydrochloric acid and water in this order
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. customto give a crude product

Sources & evidence

ORD record
ord-88ad200acb054ac08fcf4087bcbb9cfb
Source dataset
uspto-grants-2002_09
Patent number
US06448444B1

Reaction notes

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