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

HRID 1108168노트

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HRID 1108168 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
-20 °C

실험 절차

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. Yield: 10.7 g (89%).

후처리

  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

출처 및 근거

ORD 기록
ord-d439a2bb7b2f47d980e742edd70bf0df
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06063360

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