1,1-Dibromoethane → 2,3-Dihydro-1,4-benzodioxine-5-carbaldehyde

HRID 342096

반응식

HRID 342096 반응식
[OH:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH:12](Br)[CH3:13].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[O:10]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:3]([CH:4]=[O:5])[C:2]=2[O:1][CH2:13][CH2:12]1

참가 물질

6

반응물 3

HCID 112011,1-DibromoethaneHCID 14798Sodium HydroxideHCID 905792,3-Dihydroxybenzaldehyde

생성물 1

HCID 27950332,3-Dihydro-1,4-benzodioxine-5-carbaldehyde수율 70%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

실험 절차

2,3-Dihydroxybenzaldehyde (58 g, 420 mmol) was added to a refluxing mixture of dibromoethane (107.4 g, 570 mmol), sodium hydroxide (35.7 g, 890 mmol) and tetrabutyl ammonium bromide (3 g) in water (50 mL). After heating at reflux for 4 h, the mixture was cooled and the organic layer separated, washed with base, dried over sodium sulfate and concentrated in vacuo. The residue was Kugelrohr distilled at 135° to give the product (48 g, 70%) which solidified on standing (mp 61°-62° C.). Anal. Calc'd: C, 65.85; H, 4.91; Found: C, 65.73; H, 4.86.

후처리

  1. temperatureAfter heating
  2. temperatureat reflux for 4 h
  3. temperaturethe mixture was cooled
  4. customthe organic layer separated
  5. washwashed with base
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. distillationdistilled at 135°

출처 및 근거

ORD 기록
ord-66e213bc16e043f89b3317ed31f7608b
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05856529

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