Tetrahydrofuran → 4-(2-phenylethynyl)phenol

HRID 1595951ノート

反応式

HRID 1595951 の反応式
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)(=O)C.[OH-].[Na+].O1CCCC1>C(O)(=O)C>[C:13]1([C:12]#[C:11][C:8]2[CH:7]=[CH:6][C:5]([OH:4])=[CH:10][CH:9]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11851061HCID 11851061、化合物

生成物 1

HCID 110088074-(2-phenylethynyl)phenol収率 36.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

4-(Phenylethynyl)phenyl acetate (60.6 g, 0.256 moles), 20 percent aqueous sodium hydroxide (400 mL), and tetrahydrofuran (400 mL) are added to a 2-L Erlenmeyer flask and stirred at room temperature for 5 hours. The mixture is acidified with glacial acetic acid (120 mL) until a pH of 7 is reached. The aqueous layer is removed and extracted with tetrahydrofuran. The organic layers are combined and concentrated on a rotovap to give a tan solid. The solid is heated with hexanes (700 mL) on a steam bath and the hot solution decanted from the solid. This is repeated with a second volume of hexanes (700 mL). A white solid crystallizes from the hexane solution upon cooling and is isolated by filtration and dried in vacuo to give 18 g of a white solid, mp 126° C. to 127° C. NMR analysis is consistent with the structure of the desired material.

後処理

  1. customThe aqueous layer is removed
  2. extractionextracted with tetrahydrofuran
  3. concentrationconcentrated on a rotovap
  4. customto give a tan solid
  5. customthe hot solution decanted from the solid
  6. customA white solid crystallizes from the hexane solution
  7. temperatureupon cooling
  8. customis isolated by filtration
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-2fa65a2b3f4d4e19920e541e6156fc78
出典データセット
uspto-grants-2001_09
特許番号
US06288188B1

反応ノート

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