Water → (1-Bromonaphthalen-2-yl)methanol

HRID 580914

반응식

HRID 580914 반응식
O.[C:2]([O-:5])([O-])=O.[Ca+2].[Br:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1CBr>O1CCOCC1>[Br:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[CH2:2][OH:5]

참가 물질

5

반응물 3

HCID 962WaterHCID 10112Calcium CarbonateHCID 378281-Bromo-2-(bromomethyl)naphthalene

생성물 1

HCID 13113200(1-Bromonaphthalen-2-yl)methanol수율 84.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Water (100 ml) and CaCO3 (18 g, 180 mmole) were added to a solution of 13 in dioxane (100 ml) and the mixture was refluxed for 10 hr. The solution was cooled and the dioxane was removed under reduced pressure and the mixture was acidified with 1N HCl and extracted with methylene chloride. The combined methylene chloride fractions were washed with saturated solution of NaHCO3, H2O, brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give a white solid which when crystallized from hexane afforded 7 g of 24 (84.3%). A single component was detected by TLC (100% hexane, Rf, 0; hexane/ethyl acetate 80:20, Rf, 0.5); NMR (CDCl3) d 2.1 (m, 1H, H--O), d 5.0 (s, 2H, CH2 --OH), d 7.4-8.4 (m, 6H, naphthyl); MS (HRFAB) calcd for C11H9BrO (M+Li)+ 243.0003 found 243.0003.

후처리

  1. temperaturethe mixture was refluxed for 10 hr
  2. temperatureThe solution was cooled
  3. customthe dioxane was removed under reduced pressure
  4. extractionextracted with methylene chloride
  5. washThe combined methylene chloride fractions were washed with saturated solution of NaHCO3, H2O, brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customto give a white solid which when
  9. customcrystallized from hexane

출처 및 근거

ORD 기록
ord-2d0ebb2be6404c6681d6905b81f92abe
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919797

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