Hydrochloric Acid → (4-Bromophenyl)(4-methylphenyl)methanol

HRID 1181160Notes

Reaction equation

HRID 1181160 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:16])=[CH:13][CH:12]=1.Cl>C(OCC)C>[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]([C:3]2[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=2)[OH:16])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 78054-BromotolueneHCID 707414-BromobenzaldehydeHCID 5462224Magnesium

Product 1

HCID 11747838(4-Bromophenyl)(4-methylphenyl)methanolYield 306.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Magnesium turnings (0.39 g, 0.016 mol) were dried in a flask and then cooled under nitrogen. Anhydrous diethyl ether (3 mL) was added, followed by 4-bromotoluene (3.0 g, 1.8 mmol). The mixture was refluxed, and more anhydrous diethyl ether was added to keep the solution volume constant. The resultant Grignard solution was added dropwise to a solution of 4-bromobenzaldehyde (1.66 g, 9.0 mmol) in anhydrous diethyl ether(6 mL). The reaction was heated with reflux for 30 minutes, following which it was cooled. The cooled solution was poured into a solution of hydrochloric acid (HCl) (3.7 milliliters (mL) concentrated HCl in 17 grams of ice-water) and stirred for 1 hour (h). The resulting mixture was extracted with diethyl ether (3 times, 50 mL each), and the combined organic extracts were dried using magnesium sulfate (MgSO4) and concentrated in vacuo. Purification by flash chromatography on silica gel (petroleum ether/ethyl acetate, 90/10, v/v) afforded 1.53 grams of (4′-bromophenyl)-4-methylphenyl methanol, a yield of about 62% as a white solid. The melting point (mp) was 80-81° C.

Workup

  1. temperaturecooled under nitrogen
  2. temperatureThe mixture was refluxed
  3. temperatureThe reaction was heated
  4. temperaturewith reflux for 30 minutes
  5. temperaturewas cooled
  6. extractionThe resulting mixture was extracted with diethyl ether (3 times, 50 mL each)
  7. customthe combined organic extracts were dried
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel (petroleum ether/ethyl acetate, 90/10

Sources & evidence

ORD record
ord-5e38e829954d4446914bd28606affe70
Source dataset
uspto-grants-2007_10
Patent number
US07285363B2

Reaction notes

Loading…