Benzyl Chloride → 1,4-Bis(benzyloxy)-2-butene

HRID 8409

反応式

HRID 8409 の反応式
[OH-].[Na+].[CH2:3]([OH:8])[CH:4]=[CH:5][CH2:6][OH:7].[CH2:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:9]([O:7][CH2:6][CH:5]=[CH:4][CH2:3][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 7503Benzyl ChlorideHCID 80652-Butene-1,4-diolHCID 14798Sodium Hydroxide

生成物 1

HCID 40541091,4-Bis(benzyloxy)-2-butene収率 114.5%

試薬・触媒・溶媒 1

HCID 74236Tetrabutylammonium Bromide触媒

反応条件

温度
60 °C

実験手順

To 48% aqueous sodium hydroxide (127.8 g) was added tetra-n-butylammonium bromide (3.3 g, 10 mmol). The mixture was heated to 60° C. To the mixture was added 2-butene-1,4-diol (17) (30.0 g, 340 mmol), to which was added dropwise benzyl chloride (94.8 g, 743 mmol) at 80±15° C. The mixture was stirred at the same temperature for 2 hours. The reaction mixture was cooled down, and separated after the addition of water (90 ml). To the organic layer was added sulfuric acidic brine. The solution was neutralized by aqueous sodium hydrogen carbonate, separated, mixed with ethyl acetate and concentrated under reduced pressure to yield the objective (18) (104.5 g, quantitative) as an oil residue.

後処理

  1. temperatureThe reaction mixture was cooled down
  2. customseparated
  3. additionafter the addition of water (90 ml)
  4. additionTo the organic layer was added sulfuric acidic brine
  5. customseparated
  6. additionmixed with ethyl acetate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4caad36be5ac4269aa3917d91c05067e
出典データセット
uspto-grants-2006_08
特許番号
US07087764B2

関連ノート

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