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

HRID 402972

반응식

HRID 402972 반응식
[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

참가 물질

8

반응물 5

HCID 313Hydrochloric Acid2회HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 819842-Hydroxy-2-methyl-1-phenylpropan-1-oneHCID 6451240Aluminum(III) Chloride

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

반응 조건

온도
4 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-61a130eaae824248a8fd964ff58c0a7c
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742175B2

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