Bromobenzene → 7-Phenoxy-1-tetralone

HRID 376894

반응식

HRID 376894 반응식
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][CH2:14][C:15]2=[O:18])=[CH:10][CH:9]=1.Br[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1.[Cu]=O>[O:7]([C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][CH2:14][C:15]2=[O:18])=[CH:10][CH:9]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

6

반응물 3

HCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 5718187-hydroxy-3,4-dihydro-2H-naphthalen-1-one

생성물 1

HCID 43187537-Phenoxy-1-tetralone수율 78.6%

시약·촉매·용매 2

HCID 14829Copper oxide촉매HCID 1049Pyridine용매

반응 조건

온도
40 °C

실험 절차

A suspension of 60.8 g potassium carbonate in 300 ml of dry pyridine was treated with 35.7 g 7-hydroxy-3,4-dihydro-2H-naphthalen-1-one, and the mixture was heated to 40° C. Thereafter, 19.9 g copper(II) oxide was added thereto with stirring, followed by the drop-wise addition of 39.6 g bromobenzene. The reaction mixture was heated for 4 days under reflux. After evaporating the pyridine completely under vacuum, the residue was stirred with 200 ml ethyl acetate and was filtered through silica gel. The filtrate was washed with saturated solutions of ammonium chloride and sodium chloride, dried over sodium sulfate and concentrated by evaporation under vacuum. The residue was purified by column chromatography, using n-hexane/ethyl acetate as the elutant, whereupon 41.2 g (78.6% of theoretical) 7-phenoxy-3,4-dihydro-2H-naphthalen-1-one was obtained.

후처리

  1. temperatureThe reaction mixture was heated for 4 days
  2. temperatureunder reflux
  3. customAfter evaporating the pyridine completely under vacuum
  4. stirringthe residue was stirred with 200 ml ethyl acetate
  5. filtrationwas filtered through silica gel
  6. washThe filtrate was washed with saturated solutions of ammonium chloride and sodium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated by evaporation under vacuum
  9. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-0f1870388fd140ee8c997c5a0bd311e2
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06022895

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