Ethylene carbonate → 2-[4'-Fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethanol

HRID 2225797Notes

Reaction equation

HRID 2225797 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([OH:17])=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.C1(=O)O[CH2:21][CH2:20][O:19]1>[I-].C([N+](CC)(CC)CC)C.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([CH3:15])[CH3:16])[C:9]=2[O:17][CH2:21][CH2:20][OH:19])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7303Ethylene carbonateHCID 146639662-(p-Fluorophenyl)-6-isopropylphenol

Product 1

HCID 190044172-[4'-Fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethanolYield 26%

Reagents, catalysts & solvents 2

HCID 6225Tetraethylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 4'-fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-ol (1.84 g), ethylene carbonate (0.78 g) and tetraethylammonium iodide (0.68 g) was heated in an oil bath at 155° C. for 2 hours, then was cooled and taken up in dichloromethane. The solution was washed in turn with water, 1N sodium hydroxide, 1N hydrochloric acid and brine, then was dried (MgSO4) and evaporated. The residual material was chromatographed over 70 g of silica gel (ethyl acetate-hexane; 3:7) to provide 0.57 g of 2-[4'-fluoro-3-(1-methylethyl)[1,1'-biphenyl]-2-yloxy]ethanol. The compound was crystallized from hexane to give the analytical sample, mp 77°-78° C.

Workup

  1. temperaturewas cooled
  2. washThe solution was washed in turn with water, 1N sodium hydroxide, 1N hydrochloric acid and brine
  3. dry with materialwas dried (MgSO4)
  4. customevaporated
  5. customThe residual material was chromatographed over 70 g of silica gel (ethyl acetate-hexane; 3:7)

Sources & evidence

ORD record
ord-8063b8bd046e43a5a5f68fc3ef2b7a3a
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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