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

HRID 402972

反応式

HRID 402972 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

反応条件

温度
4 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-61a130eaae824248a8fd964ff58c0a7c
出典データセット
uspto-grants-2014_06
特許番号
US08742175B2

関連ノート

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