Sulfuric Acid → Benzene, 1-(4-fluorophenoxy)-3-((2-(4-fluorophenyl)-2-methylbutoxy)methyl)-

HRID 1589446Notes

Reaction equation

HRID 1589446 reaction equation
C1(C)C=CC=CC=1.S(=O)(=O)(O)O.[F:13][C:14]1[CH:28]=[CH:27][C:17]([O:18][C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[CH2:22][OH:23])=[CH:16][CH:15]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]([CH3:41])([CH2:39][CH3:40])[CH2:37]O)=[CH:32][CH:31]=1>O>[F:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]([CH3:41])([CH2:39][CH3:40])[CH2:37][O:23][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[C:19]([O:18][C:17]3[CH:27]=[CH:28][C:14]([F:13])=[CH:15][CH:16]=3)[CH:20]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 10584901[3-(4-Fluorophenoxy)phenyl]methanolHCID 155826502-(4-Fluorophenyl)-2-methylbutyl alcohol

Product 1

HCID 3067111Benzene, 1-(4-fluorophenoxy)-3-((2-(4-fluorophenyl)-2-methylbutoxy)methyl)-Yield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 20 ml of toluene were added 2 ml of concentrated sulfuric acid, 2.7 g of 3-(4-fluorophenoxy)benzyl alcohol and 2.3 g of 2-(4-fluorophenyl)-2-methylbutyl alcohol, and the mixture was refluxed for 6 hours (water formed by reaction was removed). The mixture was cooled to room temperature, and water was added to the mixture and the toluene layer was separated, washed with water, dried, and evaporated under reduced pressure, and the obtained crude ether was purified by column chromatography on 100 g of silica gel (1:1 mixed solvent of toluene and n-hexane was used as eluent) to give 2.2 g of the desired ether (the yield was 46% of the theoretical yield).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. customthe toluene layer was separated
  3. washwashed with water
  4. customdried
  5. customevaporated under reduced pressure
  6. customthe obtained crude ether
  7. customwas purified by column chromatography on 100 g of silica gel (1:1 mixed solvent of toluene and n-hexane was used as eluent)
  8. customto give 2.2 g of the desired ether (the yield was 46% of the
  9. customtheoretical yield)

Sources & evidence

ORD record
ord-84a58df6590a49dbaeea8d5003bf041b
Source dataset
uspto-grants-1986_02
Patent number
US04570005

Reaction notes

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