Hydrochloric Acid → 2-(5-Fluoro-2-hydroxyphenyl)-2-(5-fluoro-2-methoxyphenyl)propane

HRID 1413856Notes

Reaction equation

HRID 1413856 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([C:8](O)([CH3:10])[CH3:9])[CH:7]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.Cl>CCOCC>[F:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:12][CH3:13])([CH3:10])[CH3:9])[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 97324-FluorophenolHCID 222848882-(5-Fluoro-2-methoxyphenyl)propan-2-ol

Product 1

HCID 202910912-(5-Fluoro-2-hydroxyphenyl)-2-(5-fluoro-2-methoxyphenyl)propaneYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-(5-fluoro-2-methoxyphenyl)propan-2-ol (6 g) was added in small portions to a melt of 4-fluorophenol (12 g) and concentrated hydrochloric acid (10 days) at 90° C. The mixture was stirred at this temperature overnight and was then cooled and dissolved in ether. The excess of p-fluorophenol was removed by extraction with 5% aqueous sodium hydroxide solution. The alkali insoluble material crystallised from hexane to give 2-(5-fluoro-2-hydroxyphenyl)-2-(5-fluoro-2-methoxyphenyl) propane (3.9 g) as colourless prisms; m.p. 90° C.

Workup

  1. temperaturewas then cooled
  2. customThe excess of p-fluorophenol was removed by extraction with 5% aqueous sodium hydroxide solution
  3. customThe alkali insoluble material crystallised from hexane

Sources & evidence

ORD record
ord-e736f129532f4a72b644bf67ccbcaadb
Source dataset
uspto-grants-1981_02
Patent number
US04251546

Reaction notes

Loading…