Tetrahydrofuran → 3-Trifluoromethyl-4'-benzyloxy-alpha-ethyl-benzhydrol

HRID 364772Notes

Reaction equation

HRID 364772 reaction equation
[Mg].[F:2][C:3]([F:12])([F:11])[C:4]1[CH:5]=[C:6](Br)[CH:7]=[CH:8][CH:9]=1.O1CCCC1.[CH3:18][CH2:19][C:20]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:24][CH:23]=1)=[O:21]>C(O)(=O)C>[F:2][C:3]([F:12])([F:11])[C:4]1[CH:5]=[C:6]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:24][CH:23]=2)([OH:21])[CH2:19][CH3:18])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 78246p-BenzyloxypropiophenoneHCID 5462224Magnesium

Product 1

HCID 202398663-Trifluoromethyl-4'-benzyloxy-alpha-ethyl-benzhydrol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a Grignard reactant prepared from 1.46 g. of magnesium turnings and 13.5 g. of 3-trifluoromethyl-bromobenzene in 34 ml. of dry tetrahydrofurane a solution of 9.61 g. of 4-benzyloxy-propiophenone in 50 ml. of dry tetrahydrofurane is added dropwise, under moderate reflux. The reaction mixture is slightly boiled for a further hour. The progress of the reaction can be monitored by thin layer chromatography. After termination of the reaction the reaction mixture is cooled and poured onto a mixture of glacial acetic acid and ice. The solvent phase is washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent is distilled off in vacuo. 15 g. of the named compound are obtained, which can be recrystallized from n-heptane. Melting point: 50°-51° C.

Workup

  1. waitThe reaction mixture is slightly boiled for a further hour
  2. customThe progress of the reaction
  3. customAfter termination of the reaction the reaction mixture
  4. temperatureis cooled
  5. washThe solvent phase is washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent is distilled off in vacuo
  8. customof the named compound are obtained
  9. customwhich can be recrystallized from n-heptane

Sources & evidence

ORD record
ord-3b66666aee3945dea32a3c3da0eca20c
Source dataset
uspto-grants-1986_08
Patent number
US04605785

Reaction notes

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