Benzyl Bromide → Benzene, [[(12-bromododecyl)oxy]methyl]-

HRID 1289397ノート

反応式

HRID 1289397 の反応式
[H-].[Na+].O1CCCC1.[CH2:8](Br)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

7

反応物 4

HCID 7498Benzyl BromideHCID 8028Tetrahydrofuran3 回HCID 24758Sodium hydrideHCID 13789512-Bromo-1-dodecanol

生成物 1

HCID 11100339Benzene, [[(12-bromododecyl)oxy]methyl]-収率 65.7%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 962Water溶媒

実験手順

First, 2.4 g of 60% sodium hydride and 100 ml of dry tetrahydrofuran were placed in a 300 ml flask whose content was replaced with argon. Then, 15 ml of a tetrahydrofuran solution containing 11.3 g of benzyl bromide, 15 ml of a tetrahydrofuran solution containing 15.9 g of 12-bromododecanol, and 0.1 g of tetrabutylammonium iodide were added to the reaction mixture. The resultant reaction mixture was stirred under reflux for 2.5 hours. The reaction mixture was poured into water, and an organic layer was extracted with toluene. The toluene layer was washed with water and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled away. The residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/3) to obtain 14.0 g of 1-bromo-12-benzyloxydodecane (Y: 65.7%). The compound thus obtained had a purity of 98.4% by GC.

後処理

  1. additionwere added to the reaction mixture
  2. customThe resultant reaction mixture
  3. temperatureunder reflux for 2.5 hours
  4. extractionan organic layer was extracted with toluene
  5. washThe toluene layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThereafter, the solvent was distilled away
  8. customThe residue was purified by silica gel column chromatography (eluent: toluene/hexane=1/3)

出典と根拠

ORDレコード
ord-3ef41b2ced21489787fd31b062ee24c3
出典データセット
uspto-grants-1998_05
特許番号
US05750213

反応ノート

読み込み中…