Tetrahydrofuran → 4-(2-phenylethynyl)phenol

HRID 1595951노트

반응식

HRID 1595951 반응식
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

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11851061HCID 11851061, 화합물

생성물 1

HCID 110088074-(2-phenylethynyl)phenol수율 36.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2fa65a2b3f4d4e19920e541e6156fc78
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06288188B1

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