Carbon Dioxide → 2-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acid

HRID 411910

反応式

HRID 411910 の反応式
[Mg].[C:2](=[O:4])=[O:3].Cl.Br[C:7]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:21])[CH2:17][CH2:18][CH2:19][Cl:20])=[CH:12][CH:11]=1)([CH3:9])[CH3:8].ClC(C1C=CC(C(=O)CCCCl)=CC=1)(C)C>C(#N)C.[Br-].C([N+](CC)(CC)CC)C.[Ag]>[Cl:20][CH2:19][CH2:18][CH2:17][C:16]([C:13]1[CH:12]=[CH:11][C:10]([C:7]([CH3:9])([CH3:8])[C:2]([OH:4])=[O:3])=[CH:15][CH:14]=1)=[O:21]

参加物

9

反応物 5

HCID 280Carbon Dioxide2 回HCID 313Hydrochloric AcidHCID 5462224MagnesiumHCID 100635791-Butanone, 1-[4-(1-bromo-1-methylethyl)phenyl]-4-chloro-HCID 234998621-[4-(1-Chloro-1-methyl-ethyl)-phenyl)-4-chloro-butan-1-one

生成物 1

HCID 109235672-(4-(4-Chlorobutanoyl)phenyl)-2-methylpropanoic acid収率 66%

試薬・触媒・溶媒 3

HCID 6285Tetraethylammonium Bromide触媒HCID 23954Silver触媒HCID 6342Acetonitrile溶媒

実験手順

Fit a jacketed glass cell of about 50 mL capacity with an expanded silver mesh cathode (14 cm2 geometric area), a roughly concentric magnesium sacrificial anode, a tube to deliver carbon dioxide gas and a magnetic stir bar. Add a solution of hydrogen chloride remediated 1-[4-(1-bromo-1-methyl-ethyl)-phenyl]-4-chloro-butan-1-one and 1-[4-(1-chloro-1-methyl-ethyl)-phenyl]-4-chloro-butan-1-one (2.79 g, 89 mole %, 3:1 ratio of tertiary benzylic bromide to tertiary benzylic chloride by NMR, approximately 8.6 mmol total active tertiary benzylic halide) in acetonitrile (45 mL) and tetraethylammonium bromide (0.19 g). Close the cell and cool to −10° C. with a continuous carbon dioxide sparge for 169 minutes at an average current density of 13 mA cm−2. Warm to contents of the cell to ambient temperature, drain the contents, acidify with chilled aqueous 6M hydrochloric acid, extract and evaporate the solvent in vacuo to give the title compound (1.53 g, 66%).

後処理

  1. customClose the cell
  2. customsparge for 169 minutes at an average current density of 13 mA cm−2
  3. extractionextract
  4. customevaporate the solvent in vacuo

出典と根拠

ORDレコード
ord-12f44d66f4034017bf5417da798cb381
出典データセット
uspto-grants-2003_05
特許番号
US06559312B2

関連ノート

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