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

HRID 8409

반응식

HRID 8409 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 74236Tetrabutylammonium Bromide촉매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4caad36be5ac4269aa3917d91c05067e
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087764B2

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