Methanol → 1,3-Di-tert-butylbenzene

HRID 2061956Notes

Reaction equation

HRID 2061956 reaction equation
CS(O[C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:7]=1[C:16]([CH3:19])([CH3:18])[CH3:17])(=O)=O.C([O-])=O.[Li+].CO>[Pd].[C].O>[C:12]([C:9]1[CH:10]=[CH:11][CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:8]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 887MethanolHCID 23680280Lithium formateHCID 445427162,4-Di-tert-butylphenyl methanesulfonate

Product 1

HCID 1368101,3-Di-tert-butylbenzeneYield 75.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 962WaterSolvent

Procedure

Using the thus-obtained, regenerated Pd/carbon (10 g), the same reaction as in Example II-1 was carried out in a nitrogen atmosphere under normal pressure at 25° C., in which, however, 2,4-di-tert-butylphenyl methanesulfonate (100 g, 0.35 mols), lithium formate (37 g, 0.70 mols) and methanol (600 g) were used. Water (20 mL) was added to the reaction liquid and Pd/carbon was collected through filtration, and heptane (100 g) was added to the filtrate. The organic layer obtained after extraction was concentrated under reduced pressure to give crude 1,3-di-tert-butylbenzene (50 g, yield 75% by mass).

Workup

  1. customthe same reaction as in Example II-1
  2. customwas carried out in a nitrogen atmosphere under normal pressure at 25° C., in which
  3. filtrationwas collected through filtration, and heptane (100 g)
  4. additionwas added to the filtrate
  5. customThe organic layer obtained
  6. extractionafter extraction
  7. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-6c0860746d36495db6d05fdabf44a465
Source dataset
uspto-grants-2012_10
Patent number
US08283508B2

Reaction notes

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