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Water → 2-Propanone, 1-(1-oxopropoxy)-

HRID 1821141
Notes
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Reaction equation

HRID 1821141 reaction equation
[OH:1][CH2:2][C:3](=[O:5])[CH3:4].N1C=CC=CC=1.[C:12](Cl)(=[O:15])[CH2:13][CH3:14].O>C(OCC)(=O)C>[C:12]([O:1][CH2:2][C:3](=[O:5])[CH3:4])(=[O:15])[CH2:13][CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 8299HydroxyacetoneHCID 62324Propionyl chloride

Product 1

HCID 30858602-Propanone, 1-(1-oxopropoxy)-Yield 64.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of hydroxyacetone (190 g, 2.56 mol) and pyridine (210 ml, 2.6 mol) in ethyl acetate (1 L), propionyl chloride (197 g, 2.1 mol) was added dropwise at 5° C. The reaction liquid was stirred at room temperature for one hour, and then poured into water (700 ml). After phase separation, the organic layer was washed twice with a 1−N aqueous hydrochloric acid (700 ml), twice with water (700 ml), and once with saturated brine (500 ml), and dried over magnesium sulfate. After the magnesium sulfate was filtered out, the solvent was distilled off under reduced pressure, to obtain propionyloxyacetone (177 g, 1.36 mol). The thus-obtained propionyloxyacetone was used in the next process, without further purification.

Workup

  1. customThe reaction liquid
  2. customAfter phase separation
  3. washthe organic layer was washed twice with a 1−N aqueous hydrochloric acid (700 ml), twice with water (700 ml)
  4. dry with materialonce with saturated brine (500 ml), and dried over magnesium sulfate
  5. filtrationAfter the magnesium sulfate was filtered out
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-872fdbeccd164761bf96ebf45eab2455
Source dataset
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07605276B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes