Ammonium Chloride → 1-(2,5-Dimethylphenyl)-1-(2-benzyloxyphenyl)-propan-1-ol

HRID 364775Notes

Reaction equation

HRID 364775 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Mg]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[C:25](=[O:28])[CH2:26][CH3:27].[Cl-].[NH4+]>O1CCCC1>[CH3:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[C:25]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([OH:28])[CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 36146481-(2,5-Dimethylphenyl)propan-1-oneHCID 178419625HCID 178419625, compound

Product 1

HCID 202072141-(2,5-Dimethylphenyl)-1-(2-benzyloxyphenyl)-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 100 ml. of a 1.5 molar solution of 2-benzyloxyphenyl magnesium bromide in tetrahydrofurane a solution of 24.3 g. of 2',5'-dimethyl-propiophenone in 50 ml. of dry tetrahydrofurane is added under moderate reflux. The reaction mixture is stirred under slight boiling for 30 minutes, cooled and poured onto a saturated solution of ammonium chloride in ice water. Tetrahydrofurane is distilled off under reduced pressure, and the residue is extracted with benzene. The benzene phase is washed to neutral with water, and dried over anhydrous sodium sulfate. The benzene is evaporated in vacuo and the residue is fractionated to yield 43.9 g. of the named compound, boiling at 160°-162° C./1.33 Pa.

Workup

  1. temperaturecooled
  2. distillationTetrahydrofurane is distilled off under reduced pressure
  3. extractionthe residue is extracted with benzene
  4. washThe benzene phase is washed to neutral with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe benzene is evaporated in vacuo
  7. customto yield 43.9 g

Sources & evidence

ORD record
ord-f5f4df7e37544156b93ad968980c8ddd
Source dataset
uspto-grants-1986_08
Patent number
US04605785

Reaction notes

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