Diethyl Ether → 4-Vinylbenzoic acid

HRID 428782

反応式

HRID 428782 の反応式
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][CH:4]=1)=[CH2:2].[OH-].[Na+].C(OCC)C>C1COCC1.O>[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1)=[CH2:2]

参加物

6

反応物 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 583124Methyl 4-ethenylbenzoate

生成物 1

HCID 140984-Vinylbenzoic acid収率 99.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a well-stirred solution of methyl p-vinylbenzoate (36.0 g, 0.222 mole) in THF (200 mL) was added a solution of sodium hydroxide (17.78 g, 0.444 mole) in water (200 mL) at room temperature. After stirring overnight, water (100 mL), THF (150 mL), and ethyl ether (200 mL) was added and the phases separated. The aqueous phase was acidified with a solution of concentrated hydrochloric acid (41 mL) in water (90 mL) then extracted three times with THF (500-600 mL each). The latter combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to provide 32.7 g (99.5 percent) of white solids. Proton nmr (Gemini model 300 MHz) in deuterochloroform: delta 8.08 (2H), 7.50 (2H), 6.78 (1H), 5.90 (1H), 5.41 (1H).

後処理

  1. customthe phases separated
  2. extractionthen extracted three times with THF (500-600 mL each)
  3. dry with materialThe latter combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-0aeeedd0afab4e92ac9a1d754d9a4439
出典データセット
uspto-grants-2001_11
特許番号
US06313340B1

関連ノート

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