2-(2,4,6-Trimethylphenyl)propan-2-ol → 2-Isopropenyl-1,3,5-trimethylbenzene

HRID 909700Notes

Reaction equation

HRID 909700 reaction equation
CC1C=C(C)C=C(C)C=1[Mg]Br.C1([Mg]Br)C=CC=CC=1.[C:20]1([CH3:32])[CH:25]=[C:24]([CH3:26])[CH:23]=[C:22]([CH3:27])[C:21]=1[C:28](O)([CH3:30])[CH3:29]>COC1CCCC1.C1COCC1>[CH3:30][C:28]([C:21]1[C:22]([CH3:27])=[CH:23][C:24]([CH3:26])=[CH:25][C:20]=1[CH3:32])=[CH2:29]

Participants

6

Reactant 3

HCID 2930032-(2,4,6-Trimethylphenyl)propan-2-olHCID 178418255HCID 178418255, compoundHCID 178425415HCID 178425415, compound

Product 1

HCID 5189862-Isopropenyl-1,3,5-trimethylbenzeneYield 81.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 138539Cyclopentyl methyl etherSolvent

Procedure

The same experiment as in Example 2 was carried out, except for using 45 ml (0.045 mol) of a 1 M 2,4,6-trimethylphenylmagnesium bromide solution in CPME instead of 45 ml of the 1 M phenylmagnesium bromide solution in THF. The resulting reaction mixture was analyzed by gas chromatography to confirm that 2-mesityl-2-propanol and α-methyl-2,4,6-trimethylstyrene were obtained in a yield of 81.9% and 1.6%, respectively.

Workup

  1. customThe resulting reaction mixture

Sources & evidence

ORD record
ord-b5bd2f4601d54bd7a4331f3b0adff506
Source dataset
uspto-grants-2011_09
Patent number
US08017813B2

Reaction notes

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