4-Methylbenzaldehyde → 4,4'-Dimethylbenzhydrol

HRID 1388238Notes

Reaction equation

HRID 1388238 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Mg].[C:10]1([CH3:18])[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][CH:11]=1.[NH4+].[Cl-]>CCOCC>[CH3:18][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([OH:17])[C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 77254-MethylbenzaldehydeHCID 78054-BromotolueneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 2793564,4'-Dimethylbenzhydrol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To the Grignard reagent prepared from 47.2 g of p-bromotoluene and 7.2 g of magnesium in 200 ml of ether was added dropwise 30 g of p-tolualdehyde in 50 ml of ether with cooling. When the addition was complete the reaction was refluxed for 15 minutes, cooled in ice, and 40 ml of saturated NH4Cl solution was added dropwise. The reaction was filtered and the ether was removed under reduced pressure to give a yellow oil which crystallized on standing. Recrystallization from petroleum ether gave 26.1 g of nearly colorless 4,4'-dimethylbenzhydrol, m.p. 70°-71°.

Workup

  1. temperaturewith cooling
  2. additionWhen the addition
  3. temperaturewas refluxed for 15 minutes
  4. temperaturecooled in ice
  5. filtrationThe reaction was filtered
  6. customthe ether was removed under reduced pressure
  7. customto give a yellow oil which
  8. customcrystallized
  9. customRecrystallization from petroleum ether

Sources & evidence

ORD record
ord-eded33a31df840339029e1e179d3e59a
Source dataset
uspto-grants-1984_02
Patent number
US04431497

Reaction notes

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