Diethyl Ether → 1-(2-Methylphenyl)-1-phenyl-1-propanol

HRID 839304Notes

Reaction equation

HRID 839304 reaction equation
[Mg:1].[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:9][CH:10](C)[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].[Cl-].[NH4+].[CH3:22]COCC>>[C:13]1([Mg:1][Br:2])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:22][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:11]([CH2:10][CH3:9])([OH:12])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 5

HCID 3283Diethyl Ether2×HCID 7961BromobenzeneHCID 25517Ammonium ChlorideHCID 69144IsobutyrophenoneHCID 5462224Magnesium

Product 2

HCID 212663251-(2-Methylphenyl)-1-phenyl-1-propanolHCID 178418255HCID 178418255, compound

Conditions

Temperature
-5 °C

Procedure

Phenyl magnesium bromide is prepared from 14.5 g. of magnesium turnings and 80 g. of bromobenzene in 200 ml. of dry ether. the Grignard solution is cooled to -5° C, and a solution of 71 g. of 2-methyl-propiophenone in 100 ml. of ether is added under vigorous stirring. The mixture is refluxed for 15 minutes, thereafter cooled, and the Grignard complex is decomposed with an aqueous solution of ammonium chloride under cooling. The ethereal phase is separated, washed with water until neutral, and dried over anhydrous magnesium sulfate. The solvent is evaporated, and the residue is subjected to fractional distillation. This way 84.7 g. of 2-methyl-α-ethyl-benzhydrol are obtained; b.p.: 109°-113° C 0.05-0.1 mmHg.

Workup

  1. temperatureThe mixture is refluxed for 15 minutes
  2. temperaturecooled
  3. temperatureunder cooling
  4. customThe ethereal phase is separated
  5. washwashed with water until neutral, and
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent is evaporated
  8. distillationthe residue is subjected to fractional distillation

Sources & evidence

ORD record
ord-dc7b6ca53ab442a69d3b78d4bb106971
Source dataset
uspto-grants-1978_06
Patent number
US04094908

Reaction notes

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