Lithium hydroxide, monohydrate → 1,3-Dicarboxybicyclo[3.2.1]octane

HRID 1175829ノート

反応式

HRID 1175829 の反応式
[C:1]([C:5]12[CH2:12][CH:9]([CH2:10][CH2:11]1)[CH2:8][CH:7]([C:13]([O:15]C)=[O:14])[CH2:6]2)([O:3]C)=[O:2].O.[OH-].[Li+]>O1CCCC1.C(O)(C)C.O>[C:1]([C:5]12[CH2:12][CH:9]([CH2:10][CH2:11]1)[CH2:8][CH:7]([C:13]([OH:15])=[O:14])[CH2:6]2)([OH:3])=[O:2]

参加物

6

反応物 2

HCID 168937Lithium hydroxide, monohydrateHCID 684229871,3-Dicarbomethoxybicyclo[3.2.1]octane

生成物 1

HCID 684249611,3-Dicarboxybicyclo[3.2.1]octane収率 86.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A stirred solution of 1,3-dicarbomethoxybicyclo[3.2.1]octane (8.26 g, 36.5 mmol) in tetrahydrofuran (50 mL) and isopropanol (16 mL) was treated with a solution of lithium hydroxide hydrate (4.20 g, 100 mmol) in water (50 mL), and the mixture was heated to 60°-70° C. for 2 h with stirring. The organic solvents were removed in vacuo, and the alkaline aqueous solution was cooled on an ice bath and acidified with concentrated hydrochloric acid (10 mL). The solid was filtered, rinsed with cold water, and partially air dried overnight, then further dried under vacuum, triturated from acetonitrile, and redried in vacuo to afford 6.25 g (86%) of subject material as a white solid. No MS could be obtained. 1H NMR (CDCl3+drop d6-DMSO) δ 2.15-2.25 (m, 1H), 1.95-2.05 (m, 2H), 1.40-1.70 (m, 9H).

後処理

  1. temperaturethe mixture was heated to 60°-70° C. for 2 h
  2. customThe organic solvents were removed in vacuo
  3. temperaturethe alkaline aqueous solution was cooled on an ice bath
  4. filtrationThe solid was filtered
  5. washrinsed with cold water, and partially air
  6. customdried overnight
  7. customfurther dried under vacuum
  8. customtriturated from acetonitrile
  9. customredried in vacuo

出典と根拠

ORDレコード
ord-88678b9f8592420c8511ba65c6cddb25
出典データセット
uspto-grants-2010_11
特許番号
US07842707B2

反応ノート

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