Hydrochloric Acid → 3-(2-Methylbut-3-yn-2-yl)benzoic acid

HRID 2190466ノート

反応式

HRID 2190466 の反応式
[CH3:1][C:2]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11]C)=[O:10])([CH3:5])[C:3]#[CH:4].O1CCCC1.[OH-].[Na+].Cl>CO>[CH3:5][C:2]([C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([OH:11])=[O:10])([CH3:1])[C:3]#[CH:4]

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86248523Methyl 3-(2-methylbut-3-yn-2-yl)benzoate

生成物 1

HCID 862274143-(2-Methylbut-3-yn-2-yl)benzoic acid収率 92%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

To a solution of methyl 3-(1,1-dimethylprop-2-yn-1-yl)benzoate (2.26 g, 11.2 mmol) in methanol (15 mL)/tetrahydrofuran (10 mL) was added 2N aqueous sodium hydroxide solution (11.2 mL, 22.4 mmol), and the mixture was stirred at 60° C. for 3 hr. The reaction mixture was neutralized with 6N hydrochloric acid (5 mL), 1N hydrochloric acid (50 mL) was added, and the mixture was extracted with ethyl acetate (100 mL, 20 mL). The combined organic layer was washed with saturated brine (10 and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was crystallized from ethyl acetate/hexane to give the title compound (1.94 g, 92%) as colorless crystals.

後処理

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate (100 mL, 20 mL)
  3. washThe combined organic layer was washed with saturated brine (10
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was crystallized from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-f87b3f276a424f2dba7663709638307f
出典データセット
uspto-grants-2012_12
特許番号
US08324395B2

反応ノート

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