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Hydrochloric Acid → 8-(propan-2-yl)-3,4-dihydro-2H-1-benzopyran-4-one

HRID 1819505
ノート
印刷プレビュー

反応式

HRID 1819505 の反応式
[CH:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[O:6][CH2:7][CH2:8][C:9]([OH:11])=O)([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl.CN(C=O)C>[CH:1]([C:4]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:5]=1[O:6][CH2:7][CH2:8][C:9]2=[O:11])([CH3:2])[CH3:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 167772793-[2-(Propan-2-yl)phenoxy]propanoic acid

生成物 1

HCID 231190888-(propan-2-yl)-3,4-dihydro-2H-1-benzopyran-4-one

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 6344
Dichloromethane
溶媒

反応条件

温度
-20 °C

実験手順

3-(2-Isopropylphenoxy)propionic acid (11) was dissolved in dichloromethane (30 mL), and to the mixture were added oxalyl chloride (2.1 g) and DMF (5 mL) under ice-cooling. The reaction mixture was stirred for 30 minutes and cooled at −20° C. To the reaction mixture was added aluminium chloride (4 g), and the reaction mixture was stirred at −20° C. for 2 h. To the reaction mixture was added 2N hydrochloric acid, and the reaction mixture was extracted with dicloromethane. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate=4:1) to obtain the compound (12) 2.3 g.

後処理

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred at −20° C. for 2 h
  3. extractionthe reaction mixture was extracted with dicloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-e39558ed39c74c57b61429847866e967
出典データセット
uspto-grants-2009_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07601746B2

反応ノート

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