Tetrahydrofuran → 4-(2-phenylethynyl)phenol

HRID 1739359Notes

Reaction equation

HRID 1739359 reaction equation
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

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 11851061HCID 11851061, compound

Product 1

HCID 110088074-(2-phenylethynyl)phenolYield 36.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9e9891d8caec4cb48608e02d720deae0
Source dataset
uspto-grants-1999_10
Patent number
US05965679

Reaction notes

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