Catechol → Benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester

HRID 10616

반응식

HRID 10616 반응식
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].Br[C:10](Br)([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:19]([O:18][C:16]([C:10]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:1]=2[O:2]1)=[O:17])[CH3:20]

참가 물질

5

반응물 3

HCID 289CatecholHCID 11430Potassium CarbonateHCID 69427Propanedioic acid, 2,2-dibromo-, 1,3-diethyl ester

생성물 1

HCID 12969876Benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester수율 73.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Ex-1A: Catechol (2.2 g, 20 mmol) was dissolved in acetone. Diethyl dibromomalonate (7.0 g, 22 mmol) and potassium carbonate (2.76 g) were added, and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and water was added to the residue. The residue was extracted with dichloromethane, and the organic phase was washed with brine, dried over magnesium sulfate and evaporated. Chromatography (hexanes/ethyl acetate, 4:1) gave 3.9 g of benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester. 1H-NMR (CDCl3) δ 6.90–6.97 (m, 4H), 4.37 (q, J=7 Hz, 4H), 1.32 (t, J=7 Hz, 6H).

후처리

  1. customThe solvent was removed under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionThe residue was extracted with dichloromethane
  4. washthe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

출처 및 근거

ORD 기록
ord-0fb2734542694c16affef6dddddfd246
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094801B2

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