Diethyl Ether → 4,4'-Dimethylbenzhydrol

HRID 1386574Notes

Reaction equation

HRID 1386574 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.CCOCC.C(OC(C)C)(C)C.[C:21]1([CH3:29])[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][CH:22]=1>O1CCCC1.O1CCOCC1>[CH3:29][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([OH:28])[C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=2)=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 3283Diethyl Ether2×HCID 77254-MethylbenzaldehydeHCID 78054-BromotolueneHCID 7914Diisopropyl Ether

Product 1

HCID 2793564,4'-Dimethylbenzhydrol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

With reference to FIG. 1, the preferred alcohol is synthesized via a Grignard reaction. First, the magnesium salt of 4-bromotoluene, the Grignard reagent, is prepared in an anhydrous non-nucleophilic ether-based solvent. Examples of suitable solvents include, but are not limited to, diethyl ether, diisopropylether, dioxane and tetrahydrofuran. The preferred solvent is tetrahydrofuran. After preparation of the Grignard reagent, para-tolualdehyde was added to the room temperature solution of the magnesium salt at a rate sufficient to create a reflux. A sufficient time was allowed for the addition of the Grignard reagent to the aldehyde derivative, then the reaction was quenched with a proton source. Following work up of the reaction mixture, 4,4′- dimethylbenzhydrol is isolated (compound I).

Workup

  1. customWith reference to FIG. 1, the preferred alcohol is synthesized via a Grignard reaction
  2. customthe reaction was quenched with a proton source

Sources & evidence

ORD record
ord-b0608888c2bf4a76bdf3b66f8f74281e
Source dataset
uspto-grants-2001_07
Patent number
US06265559B1

Reaction notes

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