Benzyl Bromide → 4-Benzyloxyphenylacetonitrile

HRID 398025

반응식

HRID 398025 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[CH2:11]([O:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 265484-Hydroxybenzyl cyanide

생성물 1

HCID 5228044-Benzyloxyphenylacetonitrile수율 358.3%

시약·촉매·용매 2

HCID 180Acetone용매HCID 8857Ethyl Acetate용매

실험 절차

4-Hydroxybenzyl cyanide (2.5 g, 18.77 mmol), benzyl bromide (3.8 g, 22:5 mmol) and potassium carbonate (45 mmol) were combined in acetone (50 mL) and heated to reflux for 8 h. The reaction was allowed to cool to rt, diluted with ethyl acetate and filtered to remove the solids. The organic layer was concentrated in vacuo to give an oil. The crude benzyl ether was purified by chromatography on silica gel eluting hexane:ethyl acetate (90:10, v:v) to give 4-benzyloxybenzyl cyanide (4.0 g, 95%) which solidified. MS (M+NH4)+=241.

후처리

  1. temperatureheated
  2. temperatureto reflux for 8 h
  3. filtrationfiltered
  4. customto remove the solids
  5. concentrationThe organic layer was concentrated in vacuo
  6. customto give an oil
  7. customThe crude benzyl ether was purified by chromatography on silica gel
  8. washeluting hexane:ethyl acetate (90:10, v:v)

출처 및 근거

ORD 기록
ord-bc2d91ce438746bbbad4db8247c636a0
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610731B2

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