Carbon Dioxide → 2,2,6,6-Tetramethylbenzo [1,2-d:4,5-d']-bis(1,3)dioxole-4-carboxylic Acid

HRID 2592ノート

反応式

HRID 2592 の反応式
[CH3:1][C:2]1([CH3:16])[O:6][C:5]2[CH:7]=[C:8]3[O:12][C:11]([CH3:14])([CH3:13])[O:10][C:9]3=[CH:15][C:4]=2[O:3]1.C([Li])CCC.[C:22](=[O:24])=[O:23].[OH-].[Na+]>C1COCC1.CCCCCC.O>[CH3:13][C:11]1([CH3:14])[O:10][C:9]2[C:15]([C:22]([OH:24])=[O:23])=[C:4]3[O:3][C:2]([CH3:16])([CH3:1])[O:6][C:5]3=[CH:7][C:8]=2[O:12]1

参加物

8

反応物 4

HCID 280Carbon DioxideHCID 14798Sodium HydroxideHCID 109220852,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']bis([1,3]dioxole)HCID 178418339Butyllithium

生成物 1

HCID 211891412,2,6,6-Tetramethylbenzo [1,2-d:4,5-d']-bis(1,3)dioxole-4-carboxylic Acid

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-20 °C

実験手順

2,2,6,6-Tetramethylbenzo[1,2-d:4,5-d']-bis(1,3)dioxole (10.0 g, 45.0 mmol; prepared according to WO-91/12024) was dissolved in dry THF (200 mL) under an argon atmosphere. The solution was cooled to -20° C. and n-butyllithium (20.0 mL, 50.0 mmol) in hexane was added. After attaining ambient temperature, the reaction mixture was transferred onto solid carbon dioxide (150 g) and allowed to stand overnight. Water (200 mL) was added and pH was adjusted to 10 using 2M aqueous NaOH. After washing with ether, the aqueous phase was acidified with 2M hydrochloric acid to pH 2 and extracted with ether (2*300 mL). The organic phases were dried (Na2SO4) and evaporated to give the pure product.

後処理

  1. customprepared
  2. customAfter attaining ambient temperature
  3. washAfter washing with ether
  4. extractionextracted with ether (2*300 mL)
  5. dry with materialThe organic phases were dried (Na2SO4)
  6. customevaporated
  7. customto give the pure product

出典と根拠

ORDレコード
ord-ccded561afe0424fa8a1fedcae175ed7
出典データセット
uspto-grants-1998_03
特許番号
US05728370

反応ノート

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