Carbon Dioxide → 5-Methyl-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid

HRID 260718노트

반응식

HRID 260718 반응식
Br[C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[C:3]=1[CH3:12].C([Li])CCC.CCCCCC.[C:24](=[O:26])=[O:25]>O1CCCC1.O>[CH3:12][C:3]1[C:4]2[O:9][CH2:8][CH2:7][O:6][C:5]=2[CH:10]=[CH:11][C:2]=1[C:24]([OH:26])=[O:25]

참가 물질

7

반응물 4

HCID 280Carbon Dioxide2회HCID 8058HexaneHCID 124645276-Bromo-5-methyl-2,3-dihydro-1,4-benzodioxineHCID 178418339Butyllithium

생성물 1

HCID 107029595-Methyl-2,3-dihydro-1,4-benzodioxine-6-carboxylic acid수율 77%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

In 300 ml of dry tetrahydrofuran, was dissolved 32.0 g of 6-bromo-5-methyl-1,4-benzodioxane and after cooling the solution to -78° C., 96.7 ml of n-butyl lithium (n-hexane solution)was added dropwise over 20 minutes or more. After stirring at the same temperature for 1.5 hours, the reaction mixture was poured onto crushed dry ice and dry ice was sublimated while stirring. Water was added to the -mixture and the tetrahydrofuran was removed under reduced pressure. The resulting alkaline aqueous solution was washed with methylene chloride and adjusted to pH 3 with a 5% hydrochloric acid, and the precipitated crystals were collected by filtration and dried to obtain 20.9 g of 5-methyl-1,4-benzodioxan-6-carboxylic acid (yield: 77%).

후처리

  1. additionthe reaction mixture was poured
  2. stirringwhile stirring
  3. customthe tetrahydrofuran was removed under reduced pressure
  4. washThe resulting alkaline aqueous solution was washed with methylene chloride
  5. filtrationthe precipitated crystals were collected by filtration
  6. customdried

출처 및 근거

ORD 기록
ord-266f65c38c6d41cfbdb52275a0f7a04a
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05530021

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