Benzyl Bromide → 1-Benzyl-2,5-dimethoxy-3,4,6-trimethylbenzene

HRID 1646816

反応式

HRID 1646816 の反応式
C([Li])CCC.CCCCCC.Br[C:13]1[C:18]([CH3:19])=[C:17]([O:20][CH3:21])[C:16]([CH3:22])=[C:15]([CH3:23])[C:14]=1[O:24][CH3:25].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[CH2:26]([C:13]1[C:18]([CH3:19])=[C:17]([O:20][CH3:21])[C:16]([CH3:22])=[C:15]([CH3:23])[C:14]=1[O:24][CH3:25])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

6

反応物 4

HCID 7498Benzyl BromideHCID 8058HexaneHCID 2973651-Bromo-2,5-dimethoxy-3,4,6-trimethylbenzeneHCID 178418339Butyllithium

生成物 1

HCID 190880201-Benzyl-2,5-dimethoxy-3,4,6-trimethylbenzene収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A 24.1 ml (38.6 mmole) of n-butyllithium.hexane solution was added dropwise to 10.0 g (38.6 mmole) of 1-bromo-2,5-dimethoxy-3,4,6-trimethylbenzene dissolved in anhydrous tetrahydrofuran (100 ml), under an atmosphere of argon at -40° C. over the period of 10 minutes, followed by stirring for another 20 minutes. Then, 3.32 g (38.6×0.6 mmole) of cuprous bromide was added, followed by stirring at -40° to -20° C. for 1 hour. After addition of a solution of 6.60 g (38.6 mmole)of benzyl bromide in tetrahydrofuran (15 ml), the cooling bath was removed, the reaction solution was stirred at 70° C. for 1 hour and cooled with ice, followed by addition of 1N hydrochloric acid (50 ml) and stirring. The tetrahydrofuran was distilled off under reduced pressure, and isopropyl ether was added to the residue. The insoluble matter was filtered through a bed of Hyflo Supercell, and the isopropyl ether layer was separated out, washed with water and aqueous sodium chloride solution successively, dried (magnesium sulfate) and evaporated. The residual solution was distilled under reduced pressure to give 8.62 g (83%) of 1-benzyl-2,5-dimethoxy-3,4,6-trimethylbenzene, b.p.140°-142° C. (0.3 torr) and m.p. 70° to 71° C.

後処理

  1. stirringby stirring at -40° to -20° C. for 1 hour
  2. customthe cooling bath was removed
  3. stirringthe reaction solution was stirred at 70° C. for 1 hour
  4. temperaturecooled with ice
  5. additionfollowed by addition of 1N hydrochloric acid (50 ml)
  6. stirringstirring
  7. distillationThe tetrahydrofuran was distilled off under reduced pressure, and isopropyl ether
  8. additionwas added to the residue
  9. filtrationThe insoluble matter was filtered through a bed of Hyflo Supercell
  10. customthe isopropyl ether layer was separated out
  11. washwashed with water and aqueous sodium chloride solution successively
  12. dry with materialdried (magnesium sulfate)
  13. customevaporated
  14. distillationThe residual solution was distilled under reduced pressure

出典と根拠

ORDレコード
ord-31e41d4c65794895913db98c9a65d90c
出典データセット
uspto-grants-1993_01
特許番号
US05180742

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