Lithium hydroxide, monohydrate → cis-Cinnamic acid

HRID 2400035ノート

反応式

HRID 2400035 の反応式
[C:1]1(/[CH:7]=[CH:8]\[C:9]([O:11]C)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+]>O1CCCC1>[C:1]1(/[CH:7]=[CH:8]\[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 6428458Methyl cinnamate, (Z)-

生成物 1

HCID 5372954cis-Cinnamic acid収率 68.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (z)-3-phenylpropenoic acid, methyl ester (0.8 g, 4.9 mmol) in 20% aqueous tetrahydrofuran (5 mL) was treated with lithium hydroxide hydrate (0.42 g, 9.9 mmol) and the reaction mixture was stirred under argon at room temperature for 20 hours. It was concentrated in vacuo, diluted with water (50 mL) and extracted with dichloromethane (2×50 mL). The organic extracts were discarded and the aqueous layer was acidified to pH~3 with 1N hydrochloric acid and extracted with dichloromethane (3×100 mL). The combined extracts were dried over anhydrous magnesium sulfate and concentrated in vacuo to yield the title B compound (0.5 g). 1H NMR (CDCl3) δ11.57 (brs, 1H), 7.48 (m, 2H), 7.25 (m, 2H), 6.94 (d, J=12.2 Hz, 1H), 5.84 (d, J=12.3 Hz, 1H).

後処理

  1. concentrationIt was concentrated in vacuo
  2. additiondiluted with water (50 mL)
  3. extractionextracted with dichloromethane (2×50 mL)
  4. extractionextracted with dichloromethane (3×100 mL)
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-089036ef6f5b458399d19486fbda3cec
出典データセット
uspto-grants-1995_09
特許番号
US05453421

反応ノート

読み込み中…