Hydrochloric Acid → 2-(3,4-dichlorophenyl)pent-4-enoic Acid

HRID 2402138ノート

反応式

HRID 2402138 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:14][CH:15]=[CH2:16])[C:10]([O:12]C)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].O.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:14][CH:15]=[CH2:16])[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 11807390Methyl 2-(3,4-dichlorophenyl)pent-4-enoate

生成物 1

HCID 110102122-(3,4-dichlorophenyl)pent-4-enoic Acid

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 2-(3,4-dichlorophenyl)pent-4-enoate (2.47 g, 9.53 mmol) in tetrahydrofuran (15.0 mL) was added a solution of lithium hydroxide monohydrate (2.00 g, 47.6 mmol) in water (15.0 mL). The mixture was vigorously stirred at rt for 12 hrs. The resulting mixture was acidified by addition of 12.0 M of hydrochloric acid in water (3.97 mL, 47.6 mmol) at 0° C., and extracted with EtOAc (×3). The combined organic layer was dried and concentrated to provide 2-(3,4-dichlorophenyl)pent-4-enoic acid as a yellow syrup (2.65 g, quantitative). 1H NMR (400 MHz, CDCl3) δ 7.45-7.35 (m, 2H), 7.21-7.11 (dd, J=8.3, 2.1 Hz, 1H), 5.76-5.59 (ddt, J=17.0, 10.2, 6.8 Hz, 1H), 5.14-4.99 (m, 2H), 3.65-3.56 (t, J=7.7 Hz, 1H), 2.88-2.74 (dt, J=14.8, 7.5 Hz, 1H), 2.58-2.43 (dt, J=14.3, 6.9 Hz, 1H).

後処理

  1. extractionextracted with EtOAc (×3)
  2. customThe combined organic layer was dried
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-21463f6bcf384e3087618e7595befca1
出典データセット
uspto-grants-2014_08
特許番号
US08796271B2

反応ノート

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