Hydrochloric Acid → 1-(3-(Chloromethyl)phenyl)-2-hydroxy-2-methylpropan-1-one

HRID 402972

Reaktionsgleichung

Reaktionsgleichung von HRID 402972
[OH:1][C:2]([CH3:12])([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[Al+3].[Cl-:14].[Cl-].[Cl-].[CH2:17]=O.Cl.[OH-].[Na+]>C(Cl)(Cl)Cl.O>[Cl:14][CH2:17][C:7]1[CH:6]=[C:5]([C:3](=[O:4])[C:2]([OH:1])([CH3:12])[CH3:11])[CH:10]=[CH:9][CH:8]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric Acid2×HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 819842-Hydroxy-2-methyl-1-phenylpropan-1-oneHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 866937891-(3-(Chloromethyl)phenyl)-2-hydroxy-2-methylpropan-1-oneAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

under nitrogen atmosphere 5 grams of Darocur 1173 (2-hydroxy-2-methyl-1-phenylpropan-1-one) was mixed with 24 grams of anhydrous AlCl3 in 100 mL of dry chloroform. Upon cooling to 4° C. 4.5 grams of paraformaldehyde powder was slowly added and the resultant mixture was stirred at room temperature for 12 hrs (note that HCl gas released from the reaction was neutralized by 2N NaOH solution). The mixture was poured into water, and the precipitate generated was dissolved by adding 2N HCl solution. The organic layer thus separated was collected, and the aqueous layer was extracted with ethyl acetate for three times. The combined chloroform and ethyl acetate layer was next dried over anhydrous Na2SO4, filtered, and concentrated. The residue was loaded onto silica gel column and eluted by mixtures of hexane/ethyl acetate (V/V=15/1) to give the intermediate 1-(3-(chloromethyl)phenyl)-2-hydroxy-2-methylpropan-1-one as a light-yellow oil (33% yield).

Aufarbeitung

  1. dissolutionthe precipitate generated was dissolved
  2. customThe organic layer thus separated
  3. customwas collected
  4. extractionthe aqueous layer was extracted with ethyl acetate for three times
  5. dry with materialThe combined chloroform and ethyl acetate layer was next dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washeluted by mixtures of hexane/ethyl acetate (V/V=15/1)

Quellen und Nachweise

ORD-Eintrag
ord-61a130eaae824248a8fd964ff58c0a7c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742175B2

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