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

HRID 580914

反応式

HRID 580914 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 13113200(1-Bromonaphthalen-2-yl)methanol収率 84.3%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2d0ebb2be6404c6681d6905b81f92abe
出典データセット
uspto-grants-1999_07
特許番号
US05919797

関連ノート

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