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

HRID 881104

反応式

HRID 881104 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-540a099dc38442f4882dbff502c81059
出典データセット
uspto-grants-2015_03
特許番号
US08993600B2

関連ノート

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