Potassium Hydroxide → 2-(p-Fluorophenyl)-6-isopropylphenol

HRID 2225796Notes

Reaction equation

HRID 2225796 reaction equation
C([O:3][C:4]1[C:5]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:6][CH:7]=[CH:8][C:9]=1[CH:10]([CH3:12])[CH3:11])=O.[OH-].[K+]>C(O)C>[F:19][C:16]1[CH:15]=[CH:14][C:13]([C:5]2[C:4]([OH:3])=[C:9]([CH:10]([CH3:11])[CH3:12])[CH:8]=[CH:7][CH:6]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 190043884'-Fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-ol formate

Product 1

HCID 146639662-(p-Fluorophenyl)-6-isopropylphenolYield 106.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 4'-fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-ol formate (2 g) in ethanol (5 mL) was added a 10% solution of potassium hydroxide in ethanol (10 mL) and the reaction mixture was stirred at room temperature for 1 hour. The reaction was concentrated in vacuo, and the residue was partitioned between dichloromethane (20 mL) and 1N hydrochloric acid (20 mL). The separated aqueous layer was extracted with dichloromethane (2×20 mL), then the combined organic layers were washed with water, dried (MgSO4) and evaporated to furnish 1.9 g of 4'-fluoro-3-(1-methylethyl) [1,1'-biphenyl]-2-ol as a oil which solidified on standing. A small sample was sublimed to give the analytical specimen, mp 41°-43° C.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe residue was partitioned between dichloromethane (20 mL) and 1N hydrochloric acid (20 mL)
  3. extractionThe separated aqueous layer was extracted with dichloromethane (2×20 mL)
  4. washthe combined organic layers were washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-b3e9641edba9470eaa510319c6aa4b2b
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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