Formaldehyde → 2-(4H-benzo[d][1,3]dioxin-6-yl)acetonitrile

HRID 1008824

반응식

HRID 1008824 반응식
OC1C=CC([CH2:8][C:9]#[N:10])=CC=1.[CH2:11]=[O:12].[OH2:13].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17](S(O)(=O)=O)=[CH:16][CH:15]=1>C1(C)C=CC=CC=1>[O:12]1[C:15]2[CH:16]=[CH:17][C:18]([CH2:8][C:9]#[N:10])=[CH:19][C:14]=2[CH2:24][O:13][CH2:11]1

참가 물질

5

반응물 3

HCID 712FormaldehydeHCID 265484-Hydroxybenzyl cyanideHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 591662212-(4H-benzo[d][1,3]dioxin-6-yl)acetonitrile수율 9,757.2%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of (4-hydroxyphenyl)acetonitrile (17.3 g, 0.13 mol) in toluene (350 mL) were added paraformaldehyde (39.0 g, 0.43 mmol) and toluene-4-sulfonic acid monohydrate (2.5 g, 13 mmol) at room temperature. The reaction mixture was heated at reflux for 1 hour. Toluene was removed by evaporation. Water (150 mL) and ethyl acetate (150 mL) were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organics were washed with brine, dried over Na2SO4 and evaporated under vacuum. The residue was separated by preparative HPLC to give 2-(4H-benzo[d][1,3]dioxin-6-yl)acetonitrile (7.35 g, 32%). 1H NMR (400 MHz, CDCl3) δ 7.07-7.11 (m, 1 H), 6.95-6.95 (m, 1 H), 6.88 (d, J=11.6 Hz, 1 H), 5.24 (s, 2 H), 4.89 (s, 2 H), 3.67 (s, 2 H).

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 hour
  3. customToluene was removed by evaporation
  4. additionWater (150 mL) and ethyl acetate (150 mL) were added
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. washThe combined organics were washed with brine
  8. dry with materialdried over Na2SO4
  9. customevaporated under vacuum
  10. customThe residue was separated by preparative HPLC

출처 및 근거

ORD 기록
ord-9db149e862ce4de8baf9a0a9c8b54454
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07973038B2

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